Dimethyl Sulfoxide → Trametinib Dimethyl Sulfoxide

HRID 710589Notes

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

Reactant 2

HCID 679Dimethyl Sulfoxide

HCID 11707110Trametinib

Product 1

HCID 50992434Trametinib Dimethyl SulfoxideYield 84.1%

Procedure

Dimethyl sulfoxide (2 mL) was added to trametinib (80 mg) solids and the mixture was treated by ultrasound at 40 KHz for 5 minutes. The mixture suspension was stirred at room temperature for 7 days to crystallize and then centrifuged. The precipitate was collected and dried under reduced pressure at 40° C. for 16 hours to give trametinib dimethyl sulfoxide solvate Form M (75.8 mg, yield 84.1%).

Workup

additionthe mixture was treated by ultrasound at 40 KHz for 5 minutes
customto crystallize
customThe precipitate was collected
customdried under reduced pressure at 40° C. for 16 hours

Sources & evidence

ORD record: ord-4eaa681a8fe04d6aa41b86ef34a3b6c0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181243B2

Reaction notes

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