Acetyl chloride → HCID 178489598, compound

HRID 257602Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C@H:14]1[NH:19][CH2:18][C:17]2[N:20]=[CH:21][NH:22][C:16]=2[CH2:15]1)=[O:13].[C:23](Cl)(=[O:25])[CH3:24]>CN(C)C=O>[C:23]([N:19]1[C@H:14]([C:12]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH3:3])=[O:13])[CH2:15][C:16]2[NH:22][CH:21]=[N:20][C:17]=2[CH2:18]1)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (80% dispersion in mineral oil, 0.55 g, 18 mmol) was added to a solution of (S)-6-(2-methoxyphenyl)aminocarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine (2.00 g, 7 mmol) in anhydrous N,N-dimethylformamide (70 ml). The reaction mixture was heated to 80° C. for 30 minutes, then allowed to cool to room temperature. Acetyl chloride (1.46 g, 18 mmol) was added to the reaction mixture at 0° C. The reaction mixture was allowed to warm to room temperature, stirred overnight, and brought to pH 8. Water and N,N-dimethylformamide was distilled off under vacuum. The residue was chromatographed on silica gel with a solvent system of ammonium hydroxide/methanol/methylene chloride (1/8/92 v/v) to yield (S)-5-acetyl-6-(2-methoxyphenylaminocarbonyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine (free base) (1.13 g, 49%). The free base was converted to the hydrochloric acid salt: m.p.: 159° C.

Workup

temperatureto cool to room temperature
temperatureto warm to room temperature
distillationWater and N,N-dimethylformamide was distilled off under vacuum
customThe residue was chromatographed on silica gel with a solvent system of ammonium hydroxide/methanol/methylene chloride (1/8/92 v/v)

Sources & evidence

ORD record: ord-a44a33ff665a48e8a0df25de3bbfbc35
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262537

Reaction notes

Loading…