2-Chloro-N,N-dimethylquinazolin-4-amine → HCID 57716366, compound

HRID 1984931Notes

Reaction equation

HRID 1984931 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)=[O:26])=[CH:20][CH:19]=1>CC(O)C.C(N(CC)CC)C>[CH3:13][N:12]([CH3:14])[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:29][CH:28]=3)=[O:26])=[CH:22][CH:23]=2)[N:11]=1

Participants

5

Reactant 2

HCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineHCID 86610878HCID 86610878, compound

Product 1

HCID 57716366HCID 57716366, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-dimethyl-amine obtained in step B of example 1 (42 mg, 0.2 mmol) and biphenyl-4-carboxylic acid (4-aminomethyl-phenyl)-amide hydrochloride (49 mg, 0.14 mmol) in 2-propanol (1 mL) and triethylamine (200 μL) was stirred at reflux for 2 days. The resulting mixture was concentrated and purified by column chromatography (silica gel, CH2Cl2 to 10% 2 M NH3/MeOH in CH2Cl2) to give biphenyl-4-carboxylic acid {4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-phenyl}-amide (10 mg, 15%) as a white solid.

Workup

  1. temperatureat reflux for 2 days
  2. concentrationThe resulting mixture was concentrated
  3. custompurified by column chromatography (silica gel, CH2Cl2 to 10% 2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6adeaad2532f477097a2c5eb2a855fde
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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