Methyl iodide → 3-(1-(4-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1422656Notes

Reaction equation

HRID 1422656 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([N:18]4[CH2:23][CH2:22][C:21]([CH2:30][C:31]([CH3:33])=[CH2:32])([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[O:20][C:19]4=[O:34])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[C:35]([O-])([O-])=O.[K+].[K+].IC>C(#N)C>[CH3:35][N:4]1[CH:5]=[CH:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([N:18]4[CH2:23][CH2:22][C:21]([CH2:30][C:31]([CH3:33])=[CH2:32])([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[O:20][C:19]4=[O:34])[CH2:16][CH2:17]3)=[CH:11][CH:10]=2)=[CH:8][C:3]1=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 668695683-(1-(4-(2-Methoxypyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 509059523-(1-(4-(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-oneYield 83.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(1-(4-(2-methoxypyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (26.5 mg, 0.058 mmol), K2CO3 (16 mg, 2 equiv), iodomethane (250 μL, excess) and acetonitrile (3 mL) was heated at 90° C. for 1.5 h in the microwave oven. LC-MS found the reaction was complete. The mixture was filtered, concentrated, acidified with 5% aq HCl and purified by prep HPLC to afford the title compound (22 mg, 83%). LC-MS Method 1 tR=1.68 min, m/z=455.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-c20bbec6628d4d428d4bf8947bd4277a
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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