Methanesulfonyl chloride → HCID 178504940, compound

HRID 2194581Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[CH:13][N:12]=[C:11]([NH:27][C@H:28]3[CH2:33][CH2:32][C@@H:31]([CH3:34])[CH2:30][CH2:29]3)[N:10]=2)[CH2:3][CH2:2]1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>>[CH3:35][S:36]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[CH:13][N:12]=[C:11]([NH:27][C@H:28]3[CH2:29][CH2:30][C@@H:31]([CH3:34])[CH2:32][CH2:33]3)[N:10]=2)[CH2:5][CH2:6]1)(=[O:38])=[O:37]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 178461299HCID 178461299, compound

Product 1

HCID 178504940HCID 178504940, compoundYield 86%

Procedure

Using the procedure of Example 1 Step 5, 4-((piperidin-4-yl)methoxy)-N-(cis-4-methylcyclohexyl)-5-(4-morpholinophenyl)pyrimidin-2-amine was reacted with methanesulfonyl chloride to provide the title compound at 86% yield. 1H NMR (CDCl3, 400 MHz) 8.07 (s, 1H), 7.36 (d, 2H), 6.93 (d, 2 h), 5.20 (s, 1H), 4.23 (d, 2H), 4.07 (m, 1H), 3.89-3.83 (m, 6H), 3.21-3.18 (m, 4H), 2.76 (s, 3H), 2.67 (m, 2H), 1.90-1.24 (m, 14H), 0.94 (d, 3H); MS (ESI) m/z: Calc: 543.3 (M+). Found. 544.3 (M+1).

Sources & evidence

ORD record: ord-e8e820500e924f3295e1a6a975dca364
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334292B1

Reaction notes

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