Methanesulfonyl chloride → HCID 178504950, compound

HRID 2194575Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([CH2:5][O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[CH:11][N:10]=[C:9]([NH:25][C@H:26]3[CH2:31][CH2:30][C@@H:29]([CH3:32])[CH2:28][CH2:27]3)[N:8]=2)[CH2:2]1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>>[CH3:33][S:34]([N:1]1[CH2:2][CH:3]([CH2:5][O:6][C:7]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[CH:17][CH:18]=3)=[CH:11][N:10]=[C:9]([NH:25][C@H:26]3[CH2:31][CH2:30][C@@H:29]([CH3:32])[CH2:28][CH2:27]3)[N:8]=2)[CH2:4]1)(=[O:36])=[O:35]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 178461300HCID 178461300, compound

Product 1

HCID 178504950HCID 178504950, compoundYield 87%

Procedure

Using the procedure of Example 1 Step 5, 4-((azetidin-3-yl)methoxy)-N-(cis-4-methylcyclohexyl)-5-(4-morpholinophenyl)pyrimidin-2-amine was reacted with methanesulfonyl chloride to provide the title compound in 87% yield. 1H NMR (CDCl3, 400 MHz) 8.09 (s, 1H), 7.34 (d, 2H), 6.93 (d, 2H), 5.17 (sb, 1H), 4.50 (d, 2H), 4.08 (m, 1H), 4.01 (m, 2H), 3.87 (m, 4H), 3.82 (m, 2H), 3.17 (m, 4H), 3.05 (m, 1H), 2.66 (s, 3H), 1.85-1.55 (m, 6H), 1.80-1.40 (m, 3H), 0.94 (d, 3H); MS (ESI) m/z: Calc: 515.3 (M). Found. 516.3 (M+1).

Sources & evidence

ORD record: ord-3a6d74b56d1a40d98ecc8f38b1b633ad
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334292B1

Reaction notes

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