Maleic Anhydride → HCID 54708351, compound

HRID 348222Notes

Reaction equation

HRID 348222 reaction equation
[NH2:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10]2[N:15]([C:16](=[O:26])[C:17]=1[O:18]CC1C=CC=CC=1)[CH2:14][CH2:13][O:12][C:11]2([CH3:28])[CH3:27])=[O:7].[C:33]1(=O)[O:38][C:36](=[O:37])[CH:35]=[CH:34]1>C(O)(=O)C>[O:37]=[C:36]1[CH:35]=[CH:34][C:33](=[O:38])[N:1]1[C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10]2[N:15]([C:16](=[O:26])[C:17]=1[OH:18])[CH2:14][CH2:13][O:12][C:11]2([CH3:28])[CH3:27])=[O:7]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 21069982HCID 21069982, compound

Product 1

HCID 54708351HCID 54708351, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-(2-aminobenzyl)-3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide (0 050 g, 0.114 mmol) in acetic acid (1.5 mL) was added maleic anhydride (0.013 g, 0.131 mmol) and the reaction mixture stirred in a sealed tube at 115 C for 18 h. Acetic acid was evaporated in vacuo and the residue was purified by preparative HPLC (YMC-Pack C-18) to afford the title compound (0.013 g, 27% yield): 1H NMR (400 MHz, CDCl3) δ ppm: 8.03 (1H, broad t), 7.59 (1H, m), 7.48 (2H, m), 7.19 (1H, m), 6.92 (2H, s), 4.48 (2H, d, J=6.1 Hz), 4.04 (4H, s), 1.62 (6H, s); HRMS calcd for C21H21N4O6: 425.1461. Found 425.1451.

Workup

  1. customAcetic acid was evaporated in vacuo
  2. customthe residue was purified by preparative HPLC (YMC-Pack C-18)

Sources & evidence

ORD record
ord-4395ff5d7bb841b0a7409d71a391826c
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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