4-Cyanopyridine-2-carboxylic acid → 2-{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carbonyl}-isonicotinonitrile

HRID 340015Notes

Reaction equation

HRID 340015 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([OH:11])=O)[CH:4]=1)#[N:2].Br.Br.Br.[CH2:15]([C:17]1[C:18]([C:25]2[CH:33]=[C:32]3[C:28]([C:29]([C:34]4[NH:43][C:37]5[CH2:38][CH2:39][NH:40][CH2:41][CH2:42][C:36]=5[N:35]=4)=[N:30][NH:31]3)=[CH:27][CH:26]=2)=[CH:19][C:20]([F:24])=[C:21]([OH:23])[CH:22]=1)[CH3:16]>>[CH2:15]([C:17]1[CH:22]=[C:21]([OH:23])[C:20]([F:24])=[CH:19][C:18]=1[C:25]1[CH:33]=[C:32]2[C:28]([C:29]([C:34]3[NH:43][C:37]4[CH2:38][CH2:39][N:40]([C:9]([C:5]5[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=5)[C:1]#[N:2])=[O:11])[CH2:41][CH2:42][C:36]=4[N:35]=3)=[N:30][NH:31]2)=[CH:27][CH:26]=1)[CH3:16]

Participants

3

Reactant 2

HCID 242137694-Cyanopyridine-2-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 1362639482-{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carbonyl}-isonicotinonitrileYield 15.6%

Procedure

The title compound was prepared from 4-cyano-pyridine-2-carboxylic 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 6.5 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method B

Sources & evidence

ORD record
ord-791f757445d34a1ea90b6c5adf9d1251
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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