Methanesulfonyl chloride → N-(6-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)methanesulfonamide

HRID 1053945Notes

Reaction equation

[NH2:1][CH:2]1[CH:6]2[O:7][CH2:8][CH:9]([NH:10][C:11]3[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)[N:12]=3)[CH:5]2[O:4][CH2:3]1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:17][C:16]1[C:11]([NH:10][CH:9]2[CH:5]3[O:4][CH2:3][CH:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH:6]3[O:7][CH2:8]2)=[N:12][C:13]([NH:18][C:19]2[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=2)=[N:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N4-(6-aminohexahydrofuro[3,2-b]furan-3-yl)-5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-2,4-diamine (57.0 mg, 0.16 mmol) in dichloromethane (5 mL) were added TEA (26.2 mg, 0.26 mmol) and N,N-dimethylpyridin-4-amine (4.1 mg, 0.03 mmol). The mixture was cooled to 0° C., and methanesulfonyl chloride (28.3 mg, 0.25 mmol) was added to. The mixture was stirred at 0° C. for 30 min, and stirred at room temperature overnight. The solution was concentrated in vacuo, and the residue was purified with a silica gel column chromatography (MeOH/DCM (v/v)=1/30) to afford the target product as an off-white solid (28.0 mg, 40.2%).

Workup

stirringstirred at room temperature overnight
concentrationThe solution was concentrated in vacuo
customthe residue was purified with a silica gel column chromatography (MeOH/DCM (v/v)=1/30)

Sources & evidence

ORD record: ord-bfa37fc22e3d4488ab6e22d3d81aa414
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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