Acetyl chloride → HCID 53322116, compound

HRID 912522Notes

Reaction equation

HRID 912522 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:25]=[C:24]([C:26]#[N:27])[C:23]4[N:28]=[CH:29][NH:30][C:22]=4[CH:21]=3)=[CH:16][C:15]=2[C:31]([F:34])([F:33])[F:32])[CH2:7][CH2:6]1.[CH:35](N(C(C)C)CC)(C)C>C1COCC1>[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:25]=[C:24]([C:26]#[N:27])[C:23]4[N:28]=[CH:29][N:30]([CH3:35])[C:22]=4[CH:21]=3)=[CH:16][C:15]=2[C:31]([F:32])([F:34])[F:33])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86643519HCID 86643519, compound

Product 1

HCID 53322116HCID 53322116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.012 ml) was added dropwise to a solution of 1-methyl-(6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (25 mg) and diisopropylethylamine (0.051 ml) in THF (2 ml). The reaction mixture was stirred at room temperature for 18 hours. The product was then purified by acidic prep HPLC to give 6-(4-(2-(1-acetylpiperidine-4-yl)-ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (7.2 mg).

Workup

  1. customThe product was then purified by acidic prep HPLC

Sources & evidence

ORD record
ord-87df5fdd29604cb5967d2c2cd55884ea
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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