Methanesulfonyl chloride → HCID 68892450, compound

HRID 1396546Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH2:17])=[N:14][CH:15]=3)[N:10]([CH3:18])[N:9]=2)=[CH:4][C:3]=1[F:19].C(=O)=O.CC(C)=O.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.CCOC(C)=O>[NH2:17][C:13]1[N:12]=[C:11]2[N:10]([CH3:18])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:28]([CH3:27])(=[O:30])=[O:29])=[C:3]([F:19])[CH:4]=3)[C:16]2=[CH:15][N:14]=1

Participants

Conditions

Temperature: -10 °C

Procedure

3-(4-Amino-3-fluoro-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Example 58) (0.13 g, 0.50 mmol) is dissolved in pyridine (1.5 ml) under an inert atmosphere of argon. The reaction mixture is cooled to −10° C. (dry ice/acetone bath) then methanesulfonyl chloride (0.078 ml, 0.75 mmol) is added drop wise over a period of 15 minutes. The reaction mixture is stirred at −10° C. for 30 minutes then allowed to warm to room temperature and stirred for further 3 hours. The reaction mixture is diluted with EtOAc (100 ml) and washed with water (3×40 ml) and brine (10 ml). The organic portion is dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with hot EtOAc (plus few drops of MeOH), filtered and dried under vacuum at 50° C. for 3 hours to afford the title compound as an off-white solid.

Workup

temperatureto warm to room temperature
stirringstirred for further 3 hours
washwashed with water (3×40 ml) and brine (10 ml)
dry with materialThe organic portion is dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting solid is triturated with hot EtOAc (plus few drops of MeOH)
filtrationfiltered
customdried under vacuum at 50° C. for 3 hours

Sources & evidence

ORD record: ord-d9fe7c937a5840fc99d71897cfc782ad
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901134B2

Reaction notes

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