Methylamine → N-Methyl-2-{4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetamide

HRID 1054181Notes

Reaction equation

HRID 1054181 reaction equation
[CH3:1][NH2:2].[O:3]=[C:4]1[NH:9][C:8]2[CH:10]=[C:11]([C:14]([N:16]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][CH2:18][CH:17]3[CH2:26][C:27](OCC)=[O:28])=[O:15])[CH:12]=[CH:13][C:7]=2[O:6][CH2:5]1>CO>[CH3:1][NH:2][C:27](=[O:28])[CH2:26][CH:17]1[N:16]([C:14]([C:11]2[CH:12]=[CH:13][C:7]3[O:6][CH2:5][C:4](=[O:3])[NH:9][C:8]=3[CH:10]=2)=[O:15])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][CH2:18]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 131736322Ethyl {4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate2×

Product 1

HCID 118599697N-Methyl-2-{4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine (370 mL) was added slowly into a solution of ethyl {4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate (Intermediate 4, 10.7 g, 26.9 mmol) in MeOH (640 mL) at rt. The resulting mixture was stirred at rt for 16 h. The organic solvent was removed by evaporation under reduced pressure. The crude product was purified by re-crystallization from MeOH to afford the title compound (10.3 g, 100%) as a white power.

Workup

  1. customThe organic solvent was removed by evaporation under reduced pressure
  2. customThe crude product was purified by re-crystallization from MeOH

Sources & evidence

ORD record
ord-02d035f75f474f74ad7fd1d305db702d
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

Loading…