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

HRID 578721Notes

Reaction equation

HRID 578721 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-d3bb8eb233db46beae702753e5348a43
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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