Ammonia → 4-{3-[(4-Methoxy-benzoyl)-methyl-amino]-benzylamino}-quinazoline-8-carboxylic acid amide

HRID 474482Notes

Reaction equation

HRID 474482 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][N:11]=[C:10]2[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH3:24])[CH:18]=1)=O.[NH3:35]>CO>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]([N:23]([CH3:24])[C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[CH2:16][NH:15][C:10]2[C:9]3[C:14](=[C:5]([C:3]([NH2:35])=[O:2])[CH:6]=[CH:7][CH:8]=3)[N:13]=[CH:12][N:11]=2)=[O:34])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 667635364-{3-[(4-Methoxy-benzoyl)-methyl-amino]-benzylamino}-quinazoline-8-carboxylic acid methyl ester

Product 1

HCID 667640754-{3-[(4-Methoxy-benzoyl)-methyl-amino]-benzylamino}-quinazoline-8-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{3-[(4-Methoxy-benzoyl)-methyl-amino]-benzylamino}-quinazoline-8-carboxylic acid methyl ester from step d was dissolved in 1 ml 7N NH3 in methanol in a sealed vessel and stirred for 24 h at room temperature. The reaction mixture was evaporated and purified using preparative HPLC. The product was treated with HCl in methanol and concentrated in the SpeedVac.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified
  3. additionThe product was treated with HCl in methanol
  4. concentrationconcentrated in the SpeedVac

Sources & evidence

ORD record
ord-bb3343391bb440f8b0e52f66bf36bca3
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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