Methyl chloroformate → HCID 178501927, compound

HRID 2194568Notes

Reaction equation

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

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 178461301HCID 178461301, compound

Product 1

HCID 178501927HCID 178501927, compound

Procedure

Using the procedure of Example 1 Step 5, 4-(((R)-pyrrolidin-3-yl)methoxy)-N-(cis-4-methylcyclohexyl)-5-(4-morpholinophenyl)pyrimidin-2-amine with methyl chloroformate to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.08 (s, 1H), 7.38 (d, 2H), 6.94 (d, 2H), 5.22 (sb, 1H), 4.31 (d, 2H), 4.07 (m, 1H), 3.88 (m, 4H), 3.70 (s, 3H), 3.72-3.36 (m, 4H), 2.68 (m, 1H), 2.03 (m, 2H), 1.87-1.52 (m, 6H), 1.25 (m, 3H), 0.95 (d, 3H); MS (ESI) m/z: Found: 510.3 (M+1). Calc. 509.3 (M+).

Sources & evidence

ORD record: ord-0fa2a536f8904bf0845d183e4ae0291b
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334292B1

Reaction notes

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