Sodium Hydroxide → 2-(4-((4-(Isopropylamino)piperidin-1-yl)methyl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 591792Notes

Reaction equation

HRID 591792 reaction equation
C(N1C[CH2:8][N:7]([CH2:10][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][CH2:5]1)(C)C.[OH-].[Na+]>Cl>[CH:19]([NH:18][CH:17]1[CH2:5][CH2:6][N:7]([CH2:10][C:11]2[CH:12]=[CH:13][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:15][CH:16]=2)[CH2:8][CH2:14]1)([CH3:24])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1363480272-(4-((4-Isopropylpiperazin-1-yl)methyl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one

Product 1

HCID 1363480432-(4-((4-(Isopropylamino)piperidin-1-yl)methyl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-oneYield 42.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(4-((4-isopropylpiperazin-1-yl)methyl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.470 g, 0.98 mmol) in 2N HCl (20 mL) was refluxed for 3 days. The resulting mixture was basified with 2N NaOH and extracted with CH2Cl2. The organics were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, afforded the title compound (0.090 g, 21%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 8.12 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 6.73 (d, J=2.3 Hz, 1H), 6.53 (d, J=2.3 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H), 3.50 (s, 2H), 2.86-2.92 (m, 1H), 2.73-2.77 (m, 2H), 1.85-2.01 (m, 2H), 1.72-1.77 (m, 2H), 1.09-1.38 (m, 4H), 0.94 (d, J=6.2 Hz, 6H). ESI/APCI MS m/z 437 [M+H]+.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organics were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel
  7. washeluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-016d80ef0edf46a9ad9e9785f4665962
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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