Dimethyl Sulfoxide → Trametinib Dimethyl Sulfoxide

HRID 710592Notes

Reaction equation

HRID 710592 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([I:18])=[CH:15][C:16]=2[F:17])=[C:4]2[C:19]([N:21]([CH:35]3[CH2:37][CH2:36]3)[C:22]([N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]([NH:31][C:32]([CH3:34])=[O:33])[CH:30]=3)[C:3]=12)=[O:23])=[O:20].[CH3:38][S:39]([CH3:41])=[O:40]>>[CH3:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([I:18])=[CH:15][C:16]=2[F:17])=[C:4]2[C:19]([N:21]([CH:35]3[CH2:36][CH2:37]3)[C:22]([N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]([NH:31][C:32]([CH3:34])=[O:33])[CH:30]=3)[C:3]=12)=[O:23])=[O:20].[CH3:38][S:39]([CH3:41])=[O:40]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 11707110Trametinib

Product 1

HCID 50992434Trametinib Dimethyl SulfoxideYield 74.8%

Procedure

Dimethyl sulfoxide (3 mL) was added to trametinib (90 mg) at 50° C. with stirring to give a pale yellow solution. The solution was cooled with a rate of 10° C. per hour to 20° C., and then the mixture was stirred at 20° C. for 24 hours, Then the precipitate was collected and dried under reduced pressure at 40° C. for 20 hours to give trametinib dimethyl sulfoxide solvate Form M (75.9 mg, yield 74.8%).

Workup

  1. customto give a pale yellow solution
  2. temperatureThe solution was cooled with a rate of 10° C. per hour to 20° C.
  3. stirringthe mixture was stirred at 20° C. for 24 hours
  4. customthe precipitate was collected
  5. customdried under reduced pressure at 40° C. for 20 hours

Sources & evidence

ORD record
ord-21fc47110351470c97f02b781fb31b98
Source dataset
uspto-grants-2015_11
Patent number
US09181243B2

Reaction notes

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