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

HRID 578720Notes

Reaction equation

HRID 578720 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH3:20])[C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH3:28][O:29][C:30]([C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[CH:39][N:38]=[C:37]2Cl)=[O:31]>C(#N)C>[CH3:28][O:29][C:30]([C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[CH:39][N:38]=[C:37]2[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]([C:10](=[O:19])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH3:20])[CH:4]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17750396Methyl 4-chloroquinazoline-8-carboxylateHCID 62970261N-(3-Aminomethyl-phenyl)-4-methoxy-N-methyl-benzamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

101 mg (0.37 mmol) N-(3-Aminomethyl-phenyl)-4-methoxy-N-methyl-benzamide were dissolved in 3 ml acetonitrile and 260 μl (1.87 mmol) triethylamine. 130 mg (0.37 mmol) 4-Chloro-quinazoline-8-carboxylic acid methyl ester were added and the mixture was stirred overnight. The solvent was removed, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude product was used in the next step without further purification.

Workup

  1. customThe solvent was removed
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-bd8391eaf28d461cb55bca9d916fd34b
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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