Methanesulfonyl chloride → HCID 68504009, compound

HRID 2069465Notes

Reaction equation

[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH:23][CH:24]([CH3:26])[CH3:25])[N:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[OH:4].CCN(C(C)C)C(C)C.[S:36](Cl)([CH3:39])(=[O:38])=[O:37]>C(Cl)Cl>[OH:4][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH:23][CH:24]([CH3:26])[CH3:25])[N:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH2:2][NH:1][S:36]([CH3:39])(=[O:38])=[O:37]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of rac-2-amino-1-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol (39 mg, 0.11 mmol) and DIPEA (30 μL, 0.176 mmol) in DCM (6 mL) at 0° C. is added dropwise a solution of mesylchloride (10 μL, 0.132 mmol) in DCM (2 mL). The reaction mixture is stirred at 0° C. for 1 h, and then at rt for another hour. The reaction mixture is evaporated and purified by prep. TLC eluting with DCM/7M NH3 in MeOH 10:1 to give rac-N-(2-hydroxy-2-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl)-methanesulfonamide (19 mg) as a white solid; tR=0.89 min; [M+H]+=432.99.

Workup

waitat rt for another hour
customThe reaction mixture is evaporated
custompurified by prep

Sources & evidence

ORD record: ord-3abbd706da3a4825bea48f96e8490ea0
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

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