1,2-Thiazole-3-carboxylic acid → {2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl}-isothiazol-3-yl-methanone

HRID 2038667Notes

Reaction equation

HRID 2038667 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.Br.Br.Br.[CH2:12]([C:14]1[C:15]([C:22]2[CH:30]=[C:29]3[C:25]([C:26]([C:31]4[NH:40][C:34]5[CH2:35][CH2:36][NH:37][CH2:38][CH2:39][C:33]=5[N:32]=4)=[N:27][NH:28]3)=[CH:24][CH:23]=2)=[CH:16][C:17]([F:21])=[C:18]([OH:20])[CH:19]=1)[CH3:13]>>[CH2:12]([C:14]1[CH:19]=[C:18]([OH:20])[C:17]([F:21])=[CH:16][C:15]=1[C:22]1[CH:30]=[C:29]2[C:25]([C:26]([C:31]3[NH:40][C:34]4[CH2:35][CH2:36][N:37]([C:6]([C:3]5[CH:4]=[CH:5][S:1][N:2]=5)=[O:8])[CH2:38][CH2:39][C:33]=4[N:32]=3)=[N:27][NH:28]2)=[CH:24][CH:23]=1)[CH3:13]

Participants

3

Reactant 2

HCID 5592241,2-Thiazole-3-carboxylic acidHCID 1363339625-Ethyl-2-fluoro-4-[3-(1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

Product 1

HCID 136263957{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl}-isothiazol-3-yl-methanoneYield 25.6%

Procedure

The title compound was prepared from isothiazole-3-carboxylic acid (11 mg, 85 μmol) and 5-ethyl-2-fluoro-4-[3-(1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt (Preparation 32, 50 mg, 80 μmol) using the method of Example 8. The crude material was purified by HPLC Method B to afford 10.3 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method B

Sources & evidence

ORD record
ord-66a758d511d34d73ba085aaff283ac35
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

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