Methyl chloroformate → HCID 178501932, compound

HRID 2194574Notes

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.Cl[C:34]([O:36][CH3:37])=[O:35]>>[CH3:32][C@@H:29]1[CH2:30][CH2:31][C@H:26]([NH:25][C:9]2[N:8]=[C:7]([O:6][CH2:5][CH:3]3[CH2:2][N:1]([C:34]([O:36][CH3:37])=[O:35])[CH2:4]3)[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]=2)[CH2:27][CH2:28]1

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 178461300HCID 178461300, compound

Product 1

HCID 178501932HCID 178501932, compoundYield 83%

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 methyl chloroformate to provide the title compound at 83% yield. 1H NMR (CDCl3, 400 MHz) 8.10 (s, 1H), 7.35 (d, 2H), 6.92 (d, 2H), 5.16 (sb, 1H), 4.47 (d, 2H), 4.12-4.08 (m, 3H), 3.88-3.84 (m, 6H), 3.67 (s, 3H), 3.20-3.18 (m, 4H), 3.10-2.90 (m, 1H), 1.85-1.52 (m, 6H), 1.30-1.20 (m, 3H), 0.94 (d, 3H); MS (ESI) m/z: Calc: 495.3 (M+). Found. 496.3 (M+1).

Sources & evidence

ORD record: ord-3880b2506cd5473bb9b3f0ec52b2de76
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334292B1

Reaction notes

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