Sodium Hydroxide → HCID 178523416, compound
Reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:11])=[N:8][C:4]=2[CH:3]=1.[OH-].[Na+].[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[S:33](Cl)(=[O:35])=[O:34]>>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[S:33]([O:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:8][C:4]=2[CH:3]=1)(=[O:35])=[O:34]Participants
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 250 mg of 1-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-morpholin-4-ylethyl)urea in 16.4 cm3 of aqueous 0.1N sodium hydroxide solution are added 191 mg of 2,6-difluorobenzenesulfonyl chloride. The solution is stirred for 24 hours at a temperature in the region of 20° C. After addition of 40 mg of 2,6-difluorobenzenesulfonyl chloride, the mixture is stirred for 5 hours at a temperature in the region of 20° C. The reaction medium is placed in an ice bath and the precipitate is then filtered off by suction, washed with three times 5 cm3 of ice-cold water and dried under reduced pressure over phosphorus pentoxide. After flash chromatography on a column of silica [eluent: dichloromethane/methanol (93/7 by volume)], 167 mg of 2-{[(2-morpholin-4-ylethyl)carbamoyl]amino}-1H-benzimidazol-5-yl 2,6-difluorobenzenesulfonate are obtained in the form of a pale yellow powder, the characteristics of which are as follows:
Workup
- stirringthe mixture is stirred for 5 hours at a temperature in the region of 20° C
- customThe reaction medium is placed in an ice bath
- filtrationthe precipitate is then filtered off by suction
- washwashed with three times 5 cm3 of ice-cold water
- dry with materialdried under reduced pressure over phosphorus pentoxide
Sources & evidence
- ORD record
- ord-48f32e779afd467a89e06174f51cf53e
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110571B2
Reaction notes
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