Methyl formate → HCID 136262647, compound

HRID 591673Notes

Reaction equation

HRID 591673 reaction equation
[CH:1](OC)=[O:2].[CH3:5][O:6][C:7]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]2[C:8]=1[C:9](=[O:31])[NH:10][C:11]([C:19]1[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=1)=[N:12]2>>[CH3:5][O:6][C:7]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]2[C:8]=1[C:9](=[O:31])[NH:10][C:11]([C:19]1[CH:24]=[CH:23][C:22]([N:25]3[CH2:26][CH2:27][N:28]([CH:1]=[O:2])[CH2:29][CH2:30]3)=[CH:21][CH:20]=1)=[N:12]2

Participants

3

Reactant 2

HCID 7865Methyl formateHCID 1359390885,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one

Product 1

HCID 136262647HCID 136262647, compoundYield 99%

Procedure

A mixture of methyl formate (75 mL) and 5,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one (0.300 g, 0.82 mmol) was heated at reflux for 48 hours. The mixture was concentrated, and purified by silica gel chromatography, eluting with 1:1 CH2Cl2/92:7:1 CHCl3/MeOH/concentrated NH4OH, to afford the title compound (0.320 g, 99%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.79 (br s, 1H), 8.10-8.19 (m, 3H), 7.06 (d, J=9.1 Hz, 2H), 6.69 (d, J=2.3 Hz, 1H), 6.48 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.84 (s, 3H), 3.46-3.59 (m, 4H), 3.32-3.38 (m, 4H). APCI MS m/z 393 [M−H]−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 1:1 CH2Cl2/92:7:1 CHCl3/MeOH/concentrated NH4OH

Sources & evidence

ORD record
ord-2d75ea9dcf4b4e36b500ff66192721a3
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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