Ethanol → HCID 66918656, compound

HRID 641950Notes

Reaction equation

HRID 641950 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=[O:32])[C:14]1[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)[CH:17]=[CH:16][C:15]=1[N+:29]([O-])=O.[CH2:33](O)C>[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[C:13](=[O:32])[C:14]2[C:15](=[CH:16][CH:17]=[C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]3)[CH:19]=2)[N:29]=[CH:33]1

Participants

4

Reactant 2

HCID 702EthanolHCID 66919038HCID 66919038, compound

Product 1

HCID 66918656HCID 66918656, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of methyl 4-methyl-3-{[5-(4-isopropylpiperazin-1-yl)-2-nitrobenzoyl]amino}benzoate (10.7 g) and 10% palladium on carbon (0.3 g) in ethanol (200 ml) was agitated under a hydrogen atmosphere for 16 hours. The reaction mixture was filtered through diatomaceous earth (Celite®) and was concentrated to c.a. 100 ml. To this solution was added triethylorthoformate (4 ml) and glacial acetic acid (0.35 ml) and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was evaporated, redissolved in ethyl acetate, washed with saturated NaHCO3 solution. The organic phase was dried (magnesium sulphate) and evaporated to give methyl 4-methyl-3-[6-(4-isopropylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoate as a foam (7.57 g); NMR Spectrum: (DMSOd6) 1.00 (d, 6H), 2.15 (s, 3H), 2.59 (m, 4H), 2.68 (m, 1H), 3.24 (m, 4H), 3.85 (s, 3H), 7.45 (d, 1H), 7.60 (m, 3H), 7.95 (m, 1H), 8.00 (m, 1H), 8.05 (d, 1H); Mass Spectrum: M+H+ 421.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth (Celite®)
  2. concentrationwas concentrated to c.a
  3. additionTo this solution was added triethylorthoformate (4 ml) and glacial acetic acid (0.35 ml)
  4. stirringthe mixture was stirred at 80° C. for 16 hours
  5. customThe reaction mixture was evaporated
  6. dissolutionredissolved in ethyl acetate
  7. washwashed with saturated NaHCO3 solution
  8. dry with materialThe organic phase was dried (magnesium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-12493af0582d4069b8de73a87ce30a83
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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