Acetyl chloride → HCID 59410633, compound

HRID 912508Notes

Reaction equation

HRID 912508 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]([C:24]#[N:25])[C:21]3[N:26]=[CH:27][NH:28][C:20]=3[CH:19]=2)=[CH:14][C:13]=1[C:29]([F:32])([F:31])[F:30])[CH3:6].[CH:33](N(C(C)C)CC)(C)C>C1COCC1>[C:1]([N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]([C:24]#[N:25])[C:21]3[N:26]=[CH:27][N:28]([CH3:33])[C:20]=3[CH:19]=2)=[CH:14][C:13]=1[C:29]([F:32])([F:30])[F:31])[CH2:5][CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67100632HCID 67100632, compound

Product 1

HCID 59410633HCID 59410633, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (0.009 ml) was added dropwise to a solution of 6-(4-(3-(ethylamino)propoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (17.5 mg) and diisopropylethylamine (0.034 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 6-{4-[3-(N-acetyl-N-ethylamino)propoxy]-3-(trifluoromethyl)-phenyl}-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile. 1H NMR (MeOD) δ: 8.43 (s, 1H), 8.34-8.30 (m, 2H), 7.30 (t, 1H), 4.25-4.18 (m, 2H), 4.02 (s, 3H), 3.52-3.63 (m, 2H), 3.45 (q, 2H), 2.20-2.11 (m, 5H), 1.22+1.15 (2xt, 3H). MS m/z 446 (M+H).

Workup

  1. customThe product was then purified by acidic prep HPLC to 6-{4-[3-(N-acetyl-N-ethylamino)propoxy]-3-(trifluoromethyl)-phenyl}-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Sources & evidence

ORD record
ord-bcb5ba13bde4484db66def43f1f47465
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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