Methanesulfonyl chloride → HCID 67216203, compound
Reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].Cl.[NH2:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([O:28][CH3:29])[CH:20]=3)=[O:18])=[N:15][CH:16]=2)[CH:13]=1>N1C=CC=CC=1.Cl>[CH3:29][O:28][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[N+:25]([O-:27])=[O:26])[C:17]([C:14]1[N:12]2[CH:13]=[C:8]([NH:7][S:1]([CH3:4])(=[O:3])=[O:2])[CH:9]=[CH:10][C:11]2=[CH:16][N:15]=1)=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
0.107 ml (1.38 mmol) of mesyl chloride is added to 0.40 g (1.15 mmol) of (6-aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone hydrochloride in 10 ml of pyridine cooled to 5° C. and the mixture is allowed to return to ambient temperature and is stirred for 18 hours. The medium is taken up in 130 ml of 1N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under reduced pressure. The residue is taken up in isopropyl ether, filtered off, washed with isopropyl ether and then dried. 411 mg of a yellow solid are obtained. Melting point: 249° C.; 1H NMR (d6-DMSO): 3.14 (3H, s), 4.02 (3H, s), 7.39 (1H, d), 7.94 (1H, s), 8.02-8.11 (3H, m), 8.13 (1H, s), 9.88 (1H, s)
Workup
- customto return to ambient temperature
- extractionextracted with ethyl acetate
- washThe organic phase is washed with a saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- filtrationfiltered off
- washwashed with isopropyl ether
- customdried
Sources & evidence
- ORD record
- ord-591541e0f4d24ccb9c5794e25efb48ae
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008321B2
Reaction notes
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