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

HRID 340012Notes

Reaction equation

HRID 340012 reaction equation
Br.Br.Br.[CH2:4]([C:6]1[C:7]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([C:23]4[NH:24][C:25]5[CH2:30][CH2:29][NH:28][CH2:27][C:26]=5[N:31]=4)=[N:19][NH:20]3)=[CH:16][CH:15]=2)=[CH:8][C:9]([F:13])=[C:10]([OH:12])[CH:11]=1)[CH3:5].[S:32]1[CH:36]=[CH:35][C:34]([C:37](O)=[O:38])=[N:33]1>>[CH2:4]([C:6]1[CH:11]=[C:10]([OH:12])[C:9]([F:13])=[CH:8][C:7]=1[C:14]1[CH:22]=[C:21]2[C:17]([C:18]([C:23]3[NH:24][C:25]4[CH2:30][CH2:29][N:28]([C:37]([C:34]5[CH:35]=[CH:36][S:32][N:33]=5)=[O:38])[CH2:27][C:26]=4[N:31]=3)=[N:19][NH:20]2)=[CH:16][CH:15]=1)[CH3:5]

Participants

3

Reactant 2

HCID 5592241,2-Thiazole-3-carboxylic acidHCID 1784192405-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

Product 1

HCID 178436918{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl}-isothiazol-3-yl-methanoneYield 19.7%

Procedure

The title compound was prepared from 5-ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt (Preparation 25, 50 mg, 80 μmol) and isothiazole-3-carboxylic acid (11 mg, 80 μmol) using the same method as described in Example 1. The crude material was purified by HPLC Method A to afford 7.7 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method A

Sources & evidence

ORD record
ord-9f157bc7a44d47a285e9bf224975c655
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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