Sodium Hydroxide → HCID 136262644, compound

HRID 591667Notes

Reaction equation

HRID 591667 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[NH:25][C:24](=[O:26])[C:23]4[C:18](=[CH:19][C:20]([O:29][CH3:30])=[CH:21][C:22]=4[O:27][CH3:28])[N:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH:5]1[CH3:31])(=O)C.[OH-].[Na+]>Cl>[CH3:28][O:27][C:22]1[CH:21]=[C:20]([O:29][CH3:30])[CH:19]=[C:18]2[C:23]=1[C:24](=[O:26])[NH:25][C:16]([C:13]1[CH:14]=[CH:15][C:10]([N:7]3[CH2:8][CH2:9][NH:4][CH:5]([CH3:31])[CH2:6]3)=[CH:11][CH:12]=1)=[N:17]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135939118HCID 135939118, compound

Product 1

HCID 136262644HCID 136262644, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(4-(4-acetyl-3-methylpiperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.340 g, 0.80 mmol) in 2 N HCl (5 mL) was heated to reflux and stirred for 3 days. Then, the resulting solution was cooled to room temperature, basified with 2 N NaOH, extracted with CH2Cl2, and concentrated in vacuo. The material was purified by flash chromatography on silica gel, eluting with 50% to 100% of 92:7:1 CHCl3/MeOH/concentrate NH4OH in CH2Cl2, to afford the title compound (0.03 g, 9%). 1H NMR (300 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.08 (d, J=8.9 Hz, 2H), 6.99 (d, J=9.1 Hz, 2H), 6.67 (s, 1H), 6.46 (s, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 3.62-3.79 (m, 2H), 2.90-3.04 (m, 1H), 2.57-2.85 (m, 4H), 2.20-2.39 (m, 1H), 1.03 (d, J=6.3 Hz, 3H). ESI MS m/z 381 [M+H]+.

Workup

  1. temperatureto reflux
  2. extractionextracted with CH2Cl2
  3. concentrationconcentrated in vacuo
  4. customThe material was purified by flash chromatography on silica gel
  5. washeluting with 50% to 100% of 92:7:1 CHCl3/MeOH/
  6. concentrationconcentrate NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-288b3338373748ccbbed83be43cb180f
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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