tert-butyl 4-{4-[(2-{[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】54068

【品名】tert-butyl 4-{4-[(2-{[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate

【CA登记号】n/a

【分子式】C₂₄H₂₈N₄O₃S

【分子量】452.57748

【元素组成】C 63.69% H 6.24% N 12.38% O 10.61% S 7.09%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III), which is then condensed with (S)-alpha-methylbenzylamine (IV) to yield the glycinamide derivative (V). The acylation of (V) with 4-pyridylcarbonyl chloride affords the protected precursor (VI), which is finally deprotected to provide the target BILS 179 BS.

参考文献中间体

合成目标

【1】 Crute, J.J.; et al.; Herpes simplex virus helicase-primase inhibitors are active in animal models of human disease. Nat Med 2002, 8, 4, 386.
【2】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Thavonekham, B.; Grygon, C.A.; Crute, J.J. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Phenyl thiazole derivs. with anti-herpes virus properties. EP 0871619; JP 2000502702; US 6057451; WO 9724343 .
【3】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Crute, J.J.; Thavonekham, B.; Grygon, C. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Antiherpes virus cpds. and methods for their preparation and use. US 6288091 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	54066	tert-butyl 4-(4-aminophenyl)-1,3-thiazol-2-ylcarbamate	n/a	C₁₄H₁₇N₃O₂S	详情	详情
(II)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(III)	54067	tert-butyl 4-{4-[(2-bromoacetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₁₆H₁₈BrN₃O₃S	详情	详情
(IV)	20042	(1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine		C₈H₁₁N	详情	详情
(V)	54068	tert-butyl 4-{4-[(2-{[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₂₄H₂₈N₄O₃S	详情	详情
(VI)	27850	isonicotinoyl chloride	39178-35-3	C₆H₄ClNO	详情	详情
(VII)	54069	tert-butyl 4-{4-[(2-{isonicotinoyl[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₃₀H₃₁N₅O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III), which is then condensed with 4-pyridylmethylamine (IV) to yield the glycinamide derivative (V). The acylation of (V) with cyclohexanecarbonyl chloride affords the protected precursor (VI), which is finally deprotected to provide the target BILS 103 BS.

参考文献中间体

合成目标

【1】 Crute, J.J.; et al.; Herpes simplex virus helicase-primase inhibitors are active in animal models of human disease. Nat Med 2002, 8, 4, 386.
【2】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Thavonekham, B.; Grygon, C.A.; Crute, J.J. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Phenyl thiazole derivs. with anti-herpes virus properties. EP 0871619; JP 2000502702; US 6057451; WO 9724343 .
【3】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Crute, J.J.; Thavonekham, B.; Grygon, C. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Antiherpes virus cpds. and methods for their preparation and use. US 6288091 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	54066	tert-butyl 4-(4-aminophenyl)-1,3-thiazol-2-ylcarbamate	n/a	C₁₄H₁₇N₃O₂S	详情	详情
(II)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(III)	54067	tert-butyl 4-{4-[(2-bromoacetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₁₆H₁₈BrN₃O₃S	详情	详情
(IV)	20042	(1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine		C₈H₁₁N	详情	详情
(V)	54068	tert-butyl 4-{4-[(2-{[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₂₄H₂₈N₄O₃S	详情	详情
(VI)	17220	cyclohexanecarbonyl chloride; Cyclohexanecarboxylic acid chloride	2719-27-9	C₇H₁₁ClO	详情	详情
(VII)	54070	tert-butyl 4-[4-({2-[(cyclohexylcarbonyl)(4-pyridinylmethyl)amino]acetyl}amino)phenyl]-1,3-thiazol-2-ylcarbamate	n/a	C₂₉H₃₅N₅O₄S	详情	详情

Extended Information