Acetyl chloride → HCID 46842551, compound

HRID 912506Notes

Reaction equation

HRID 912506 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][N:6]1[C:14]2[CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][NH:25][CH3:26])=[C:17]([C:27]([F:30])([F:29])[F:28])[CH:16]=3)[N:11]=[C:10]([C:31]#[N:32])[C:9]=2[N:8]=[CH:7]1.C(N(C(C)C)CC)(C)C>C1COCC1>[C:1]([N:25]([CH2:24][CH2:23][CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[C:10]([C:31]#[N:32])[C:9]3[N:8]=[CH:7][N:6]([CH3:5])[C:14]=3[CH:13]=2)=[CH:16][C:17]=1[C:27]([F:30])([F:29])[F:28])[CH3:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 59410673methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 46842551HCID 46842551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.011 ml) was added dropwise to a solution of 1-methyl-6-(4-(3-(methylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (20 mg) and diisopropylethylamine (0.045 ml) in THF (2 ml). The reaction mixture was stirred at room temperature for 1 hour. The product was then purified by acidic prep HPLC to give 6-{-4-[3-(N-acetyl-N-methylamino)propoxy]-3-(trifluoromethyl)phenyl}-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (9.2 mg).

Workup

  1. customThe product was then purified by acidic prep HPLC

Sources & evidence

ORD record
ord-8a246596a653448281d8288e2a3b3c09
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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