Methanesulfonic Acid → Dabrafenib Mesylate

HRID 590152Notes

Reaction equation

HRID 590152 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:35])=[C:19]([NH:23][S:24]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38]>C(O)(C)C>[CH3:36][S:37]([OH:40])(=[O:39])=[O:38].[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:14])([CH3:15])[CH3:16])=[N:10][C:9]=2[C:17]2[C:18]([F:35])=[C:19]([NH:23][S:24]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 44462760Dabrafenib

Product 1

HCID 44516822Dabrafenib MesylateYield 86.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (204 mg, 0.393 mmol) in isopropanol (2 mL), methanesulfonic acid (0.131 mL, 0.393 mmol) was added and the solution was allowed to stir at room temperature for 3 hours. A white precipitate formed and the slurry was filtered and rinsed with diethyl ether to give the title product as a white crystalline solid (210 mg, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.85 (s, 1H) 7.92-8.05 (m, 1H) 7.56-7.72 (m, 1H) 6.91-7.50 (m, 7H) 5.83-5.98 (m, 1H) 2.18-2.32 (m, 3H) 1.36 (s, 9H). MS (ESI): 520.0 [M+H]+.

Workup

  1. customA white precipitate formed
  2. filtrationthe slurry was filtered
  3. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-e05b135182f74905b3122904ce0634a3
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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