Dimethyl Sulfoxide → N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide
Reaction equation
C(N(CC)CC)C.CS(C)=O.[OH:12][CH2:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:40])[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:28][CH:27]=3)=[CH:20][N:19]2[C:41]=1[CH3:42]>O>[CH3:42][C:41]1[N:19]2[CH:20]=[C:21]([NH:24][C:25](=[O:40])[C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:30][CH:31]=3)[CH:22]=[CH:23][C:18]2=[N:17][C:16]=1[CH2:15][CH2:14][CH:13]=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylamine (87.9 μL) and sulfur trioxide-pyridine complex (46.3 mg) were added to a DMSO solution (3 mL) of the compound (20.0 mg) obtained in Example 14, at room temperature. After stirred for 11 hours, the reaction liquid was poured into saturated saline water, and extracted with chloroform. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel chromatography (methanol/chloroform=1/25 to 1/8) to obtain N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide (10.8 mg).
Workup
- customthe reaction liquid
- extractionextracted with chloroform
- dry with materialThe organic layer was dried with sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified through silica gel chromatography (methanol/chloroform=1/25 to 1/8)
Sources & evidence
- ORD record
- ord-735b33487d054610a492fbf6682aca76
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07566781B2
Reaction notes
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