Ammonium Acetate → HCID 21913125, compound
Reaction equation
[C:1]([O-])(=O)[CH3:2].[NH4+:5].[C:6]1([S:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:28]3[C:27]([CH3:29])=[C:26]([CH3:30])[N:25]=[C:24](OC4C=CC=CC=4)[C:23]=3[N:22]=[C:21]2[CH2:38]CC)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[C:6]1([S:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[C:28]3[C:27]([CH3:29])=[C:26]([CH3:30])[N:25]=[C:24]([NH2:5])[C:23]=3[N:22]=[C:21]2[CH2:38][CH2:1][CH3:2])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
Ammonium acetate (18 g, 0.23 mol) and 1-[5-(benzenesulfonyl)pentyl]-6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridine (1.74 g, 3.54 mmol) were heated at 165° C. in a sealed tube for 8 hours with stirring. Following the work-up, an analysis by NMR indicated that starting material was present; additional ammonium acetate was added (18 g, 0.23 mol), and the reaction was continued overnight at 160° C. The solution was allowed to cool to room temperature and partitioned between chloroform (100 mL) and 1 M sodium hydroxide (75 mL). Following the work-up, the crude product (1.37 g) was purified by column chromatography on silica gel (eluting with 97:3:0.1 dichloromethane:methanol:ammonium hydroxide) and then recrystallized from acetonitrile to provide 0.715 g of 1-[5-(benzenesulfonyl)pentyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 134.0–136.0° C. with a phase change at 122–125° C.
Workup
- custompartitioned between chloroform (100 mL) and 1 M sodium hydroxide (75 mL)
- customthe crude product (1.37 g) was purified by column chromatography on silica gel (eluting with 97:3:0.1 dichloromethane:methanol:ammonium hydroxide)
- customrecrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-c775be0e3d8043e4a528a7cf1d13657a
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07220758B2
Reaction notes
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