Sodium Hydroxide → HCID 135939117, compound

HRID 591645Notes

Reaction equation

HRID 591645 reaction equation
C([N:4]1[CH:9]([CH3:10])[CH2:8][N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[NH:26][C:25](=[O:27])[C:24]4[C:19](=[CH:20][C:21]([O:30][CH3:31])=[CH:22][C:23]=4[O:28][CH3:29])[N:18]=3)=[CH:13][CH:12]=2)[CH2:6][CH:5]1[CH3:32])(=O)C.[OH-].[Na+]>Cl>[CH3:10][C@H:9]1[NH:4][C@@H:5]([CH3:32])[CH2:6][N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[NH:26][C:25](=[O:27])[C:24]4[C:19](=[CH:20][C:21]([O:30][CH3:31])=[CH:22][C:23]=4[O:28][CH3:29])[N:18]=3)=[CH:13][CH:12]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136415073HCID 136415073, compound

Product 1

HCID 135939117HCID 135939117, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(4-(4-acetyl-3,5-dimethylpiperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.150 g, 0.34 mmol) in 2N HCl was heated at reflux temperature for 3 days. The reaction was cooled to room temperature, basified with 1N NaOH, and extracted with CH2Cl2. Purification by flash chromatography on silica gel, eluting with 0% to 15% MeOH/CH2Cl2, followed by further purification, eluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH, afforded the title compound (0.040 g, 30%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.98 (br s, 1H), 8.08 (d, J=9.0 Hz, 2H), 7.00 (d, J=9.0 Hz, 2H), 6.68 (d, J=2.3 Hz, 1H), 6.46 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 3.73-3.76 (m, 2H), 2.78-2.81 (m, 2H), 2.19-2.26 (m, 2H), 1.03 (d, J=6.2 Hz, 6H). ESI MS m/z 395 [M+H]+.

Workup

  1. temperatureat reflux temperature for 3 days
  2. extractionextracted with CH2Cl2
  3. customPurification by flash chromatography on silica gel
  4. washeluting with 0% to 15% MeOH/CH2Cl2
  5. customfollowed by further purification
  6. washeluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH

Sources & evidence

ORD record
ord-6616f10b333943ba9e1c21256a6b0ce6
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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