A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones

Lan Ying Qin; Andrew G. Cole; Axel Metzger; Marc Raleigh Brescia; Kurt W. Saionz; Joan J. Zhang; Pascal Rigollier; James R. Wareing; Hubert Gstach; Juerg Zimmermann; Roland E. Dolle; John J. Baldwin; Ian Henderson

doi:10.1016/j.tetlet.2010.06.070

A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones

Lan Ying Qin, Andrew G. Cole, Axel Metzger, Marc Raleigh Brescia, Kurt W. Saionz, Joan J. Zhang, Pascal Rigollier, James R. Wareing, Hubert Gstach, Juerg Zimmermann, Roland E. Dolle, John J. Baldwin, Ian Henderson

Center for Drug Discovery

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones is described. The synthesis was developed on solid phase and was applied to provide a series of analogs in good yield. The key reactions are acylation of a cysteine derivative with 2,4-dichloropyrimidine-5-carbonyl chloride followed by cyclization to generate a 6-arylmethyl-7-carboxamido-2-chloro-7,8-dihydropyrimido[5,4-f][1,4]thiazepin-5- one, which is further derivatized with an amine to give the desired 2-amino-6-arylmethyl-7-carboxamido-7,8-dihydropyrimido[5,4-f][1,4] thiazepin-5-one.

Original language	English
Pages (from-to)	4486-4489
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.070
State	Published - Aug 25 2010

Keywords

Dihydropyrimidothiazepinone
Solid phase

Access to Document

10.1016/j.tetlet.2010.06.070

Cite this

Qin, L. Y., Cole, A. G., Metzger, A., Brescia, M. R., Saionz, K. W., Zhang, J. J., Rigollier, P., Wareing, J. R., Gstach, H., Zimmermann, J., Dolle, R. E., Baldwin, J. J., & Henderson, I. (2010). A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones. Tetrahedron Letters, 51(34), 4486-4489. https://doi.org/10.1016/j.tetlet.2010.06.070

@article{34241b5f07ed4605a4dceaf3c86c824d,

title = "A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones",

abstract = "A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones is described. The synthesis was developed on solid phase and was applied to provide a series of analogs in good yield. The key reactions are acylation of a cysteine derivative with 2,4-dichloropyrimidine-5-carbonyl chloride followed by cyclization to generate a 6-arylmethyl-7-carboxamido-2-chloro-7,8-dihydropyrimido[5,4-f][1,4]thiazepin-5- one, which is further derivatized with an amine to give the desired 2-amino-6-arylmethyl-7-carboxamido-7,8-dihydropyrimido[5,4-f][1,4] thiazepin-5-one.",

keywords = "Dihydropyrimidothiazepinone, Solid phase",

author = "Qin, {Lan Ying} and Cole, {Andrew G.} and Axel Metzger and Brescia, {Marc Raleigh} and Saionz, {Kurt W.} and Zhang, {Joan J.} and Pascal Rigollier and Wareing, {James R.} and Hubert Gstach and Juerg Zimmermann and Dolle, {Roland E.} and Baldwin, {John J.} and Ian Henderson",

year = "2010",

month = aug,

day = "25",

doi = "10.1016/j.tetlet.2010.06.070",

language = "English",

volume = "51",

pages = "4486--4489",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "34",

}

Qin, LY, Cole, AG, Metzger, A, Brescia, MR, Saionz, KW, Zhang, JJ, Rigollier, P, Wareing, JR, Gstach, H, Zimmermann, J, Dolle, RE, Baldwin, JJ & Henderson, I 2010, 'A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones', Tetrahedron Letters, vol. 51, no. 34, pp. 4486-4489. https://doi.org/10.1016/j.tetlet.2010.06.070

TY - JOUR

T1 - A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones

AU - Qin, Lan Ying

AU - Cole, Andrew G.

AU - Metzger, Axel

AU - Brescia, Marc Raleigh

AU - Saionz, Kurt W.

AU - Zhang, Joan J.

AU - Rigollier, Pascal

AU - Wareing, James R.

AU - Gstach, Hubert

AU - Zimmermann, Juerg

AU - Dolle, Roland E.

AU - Baldwin, John J.

AU - Henderson, Ian

PY - 2010/8/25

Y1 - 2010/8/25

N2 - A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones is described. The synthesis was developed on solid phase and was applied to provide a series of analogs in good yield. The key reactions are acylation of a cysteine derivative with 2,4-dichloropyrimidine-5-carbonyl chloride followed by cyclization to generate a 6-arylmethyl-7-carboxamido-2-chloro-7,8-dihydropyrimido[5,4-f][1,4]thiazepin-5- one, which is further derivatized with an amine to give the desired 2-amino-6-arylmethyl-7-carboxamido-7,8-dihydropyrimido[5,4-f][1,4] thiazepin-5-one.

AB - A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones is described. The synthesis was developed on solid phase and was applied to provide a series of analogs in good yield. The key reactions are acylation of a cysteine derivative with 2,4-dichloropyrimidine-5-carbonyl chloride followed by cyclization to generate a 6-arylmethyl-7-carboxamido-2-chloro-7,8-dihydropyrimido[5,4-f][1,4]thiazepin-5- one, which is further derivatized with an amine to give the desired 2-amino-6-arylmethyl-7-carboxamido-7,8-dihydropyrimido[5,4-f][1,4] thiazepin-5-one.

KW - Dihydropyrimidothiazepinone

KW - Solid phase

UR - http://www.scopus.com/inward/record.url?scp=77955710894&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.06.070

DO - 10.1016/j.tetlet.2010.06.070

M3 - Article

AN - SCOPUS:77955710894

SN - 0040-4039

VL - 51

SP - 4486

EP - 4489

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this