Dimethyl Sulfoxide → HCID 86664269, compound
Reaction equation
ClCCl.CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:14][C:15]1[N:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C@@:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[CH2:26][C@H:25]2[CH2:27][OH:28])=[CH:17][N:16]=1>O.C(N(CC)CC)C>[Cl:14][C:15]1[N:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C@@:24]2([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[CH2:26][C@H:25]2[CH:27]=[O:28])=[CH:17][N:16]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A dichloromethane (25 ml) solution of dimethyl sulfoxide (5 ml) was added dropwise to a dichloromethane (100 ml) solution of oxalyl chloride (2.98 ml), while the solution was stirred at −78° C. The obtained mixture was stirred at −78° C. for 10 minutes, and a dichloromethane (25 ml) solution of the compound 323-1 (5.67 g) was then added dropwise to the reaction mixture. The obtained mixture was stirred at −78° C. for 30 minutes. Thereafter, triethylamine (14.7 ml) was added to the reaction mixture, and the obtained mixture was stirred for 2 hours, while it was heated to 0° C. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, so as to obtain the title compound (7.12 g).
Workup
- stirringThe obtained mixture was stirred at −78° C. for 10 minutes
- stirringThe obtained mixture was stirred at −78° C. for 30 minutes
- stirringthe obtained mixture was stirred for 2 hours, while it
- temperaturewas heated to 0° C
- extractionthe mixture was extracted with dichloromethane
- dry with materialThe obtained organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-352dbbdb3ad241da8e141cc81caf2e4b
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268848B2
Reaction notes
Loading…