2-Cyanopyridine-4-Carboxaldehyde → 4-{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-ylmethyl}-pyridine-2-carbonitrile

HRID 340026Notes

Reaction equation

HRID 340026 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=1)=O.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:34][C:35]5[CH2:40][CH2:39][NH:38][CH2:37][C:36]=5[N:41]=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:34][C:35]4[CH2:40][CH2:39][N:38]([CH2:1][C:3]5[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=5)[CH2:37][C:36]=4[N:41]=3)=[N:29][NH:30]2)=[CH:26][CH:25]=1)[CH3:15]

Participants

3

Reactant 2

HCID 27629892-Cyanopyridine-4-CarboxaldehydeHCID 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 1784369124-{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-ylmethyl}-pyridine-2-carbonitrileYield 24.6%

Procedure

The title compound was prepared from 4-formyl-pyridine-2-carbonitrile (26 mg, 198 μmol) and 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, 132 μmol) using the method of Example 18. The crude material was purified by HPLC Method B to afford 16 mg of the title compound.

Workup

  1. customThe crude material was purified by HPLC Method B

Sources & evidence

ORD record
ord-154789f008b648ac873f185fb9a1e528
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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