Acetyl chloride → HCID 59410650, compound

HRID 912509Notes

Reaction equation

HRID 912509 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23]([C:25]#[N:26])[C:22]3[N:27]=[CH:28][NH:29][C:21]=3[CH:20]=2)=[CH:15][C:14]=1[C:30]([F:33])([F:32])[F:31])([CH3:7])[CH3:6].[CH:34](N(C(C)C)CC)(C)C>C1COCC1>[C:1]([N:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23]([C:25]#[N:26])[C:22]3[N:27]=[CH:28][N:29]([CH3:34])[C:21]=3[CH:20]=2)=[CH:15][C:14]=1[C:30]([F:31])([F:32])[F:33])[CH:5]([CH3:7])[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67145105HCID 67145105, compound

Product 1

HCID 59410650HCID 59410650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.008 ml) was added dropwise to a solution of 6-(4-(3-(isopropylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (15 mg) and diisopropylethylamine (0.031 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-isopropylamino)propoxy]-3-(trifluoromethyl)-phenyl}-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile. 1H NMR (DMSO) δ: 8.72 (s, 1H), 8.64 (s, 1H), 8.46-8.42 (m, 2H), 7.43 (t, 1H), 3.99 (s, 3H), 3.40+3.28 (2xt, 1H), 2.04-1.96 (m, 3H), 1.16-1.10 (dd, 6H). MS m/z 460 (M+H).

Workup

  1. customThe product was then purified by acidic prep HPLC

Sources & evidence

ORD record
ord-bed1bb1403224683a1f679ce4cb89bbd
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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