4-Fluorobenzoic 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}-(4-fluoro-phenyl)-methanone

HRID 340016Notes

Reaction equation

HRID 340016 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Br.Br.Br.[CH2:14]([C:16]1[C:17]([C:24]2[CH:32]=[C:31]3[C:27]([C:28]([C:33]4[NH:42][C:36]5[CH2:37][CH2:38][NH:39][CH2:40][CH2:41][C:35]=5[N:34]=4)=[N:29][NH:30]3)=[CH:26][CH:25]=2)=[CH:18][C:19]([F:23])=[C:20]([OH:22])[CH:21]=1)[CH3:15]>>[CH2:14]([C:16]1[CH:21]=[C:20]([OH:22])[C:19]([F:23])=[CH:18][C:17]=1[C:24]1[CH:32]=[C:31]2[C:27]([C:28]([C:33]3[NH:42][C:36]4[CH2:37][CH2:38][N:39]([C:6]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=5)=[O:8])[CH2:40][CH2:41][C:35]=4[N:34]=3)=[N:29][NH:30]2)=[CH:26][CH:25]=1)[CH3:15]

Participants

3

Reactant 2

HCID 99734-Fluorobenzoic 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 136263949{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}-(4-fluoro-phenyl)-methanoneYield 35.3%

Procedure

The title compound was prepared from 4-fluoro-benzoic acid (12.5 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 14.5 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method B

Sources & evidence

ORD record
ord-36dbe5946ce34bcbb9a68595137e42b7
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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