Sodium Hydroxide → HCID 136262642, compound

HRID 591666Notes

Reaction equation

HRID 591666 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:34])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]([CH:31]([CH3:33])[CH3:32])C(=O)C)[CH2:23][CH2:22]3)=[CH:17][CH:16]=1)=[N:8]2.[OH-].[Na+]>Cl>[CH:31]([NH:27][CH:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:19]=[CH:20][C:15]([C:7]3[NH:6][C:5](=[O:34])[C:4]4[C:9](=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:3]=4[O:2][CH3:1])[N:8]=3)=[CH:16][CH:17]=2)[CH2:22][CH2:23]1)([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135939122HCID 135939122, compound

Product 1

HCID 136262642HCID 136262642, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(1-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl)piperidin-4-yl)-N-isopropylacetamide (0.130 g, 0.27 mmol) in 2 N HCl (8 mL) was heated to reflux and stirred overnight. The resulting solution was cooled to room temperature, basified with 2 N NaOH (pH 14), and extracted with CH2Cl2. The solution was concentrated in vacuo and the residue was purified by flash chromatography on silica gel, eluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, to afford the title compound (0.060 g, 52%). 1H NMR (300 MHz, DMSO-d6): δ 8.07 (d, J=9.0 Hz, 2H), 6.99 (d, J=9.1 Hz, 2H), 6.67 (s, 1H), 6.46 (s, 1H), 3.75-3.95 (m, 8H), 2.81-2.99 (m, 3H), 2.69-2.79 (m, 1H), 1.79-1.92 (m, 2H), 1.14-1.37 (m, 3H), 0.97 (d, J=6.1 Hz, 6H). ESI MS m/z 423 [M+H]+.

Workup

  1. temperatureto reflux
  2. extractionextracted with CH2Cl2
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on silica gel
  5. washeluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-346e09e836564940af2ffbc33ea5fc66
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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