Pyridine → HCID 86758998, compound
Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[NH2:14][C:15]1[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH3:22])[C:16]=1[C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1.CN([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37]N=1)C.N1C=CC=C[CH:42]=1>>[O:27]1[C:26]2[CH:30]=[CH:31][C:23]([C:16]3[C:17]([O:21][CH3:22])=[N:18][N:19]([CH3:20])[C:15]=3[N:14]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[C:37]3[CH:42]=[CH:35][CH:40]=[CH:39][CH:38]=3)=[CH:24][C:25]=2[O:29][CH2:28]1Participants
Procedure
4-Isopropylbenzenesulfonyl chloride (176 mg) was added at room temperature under an atmosphere of nitrogen to a solution of 5-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole (Preparation 43) (100 mg) and dimethylaminopyridine (50 mg) in anhydrous pyridine (4 ml). The reaction was stirred overnight. The mixture was concentrated under reduced pressure, then a saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml), and brine (6 ml) were sequentially added. The aqueous phase was extracted with ethyl acetate (2*8 ml) and the combined organic fractions were washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified to yield the title compound (11.9 mg).
Workup
- concentrationThe mixture was concentrated under reduced pressure
- additiona saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml), and brine (6 ml) were sequentially added
- extractionThe aqueous phase was extracted with ethyl acetate (2*8 ml)
- washthe combined organic fractions were washed with brine (10 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified
Sources & evidence
- ORD record
- ord-c85399f54093470aafdd4b81625f85f5
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573270B1
Reaction notes
Loading…