Cyclohexanecarboxylic acid → N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinazolinyl]-cyclohexanecarboxamide

HRID 1827271Notes

Reaction equation

HRID 1827271 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[CH:34]1([C:40](O)=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.Cl.C(C(NCCCN(C)C)=N)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1.O>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]4[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=4)([OH:20])[C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[CH:8]=3)[N:3]=[C:2]([NH:1][C:40]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:41])[N:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 7413Cyclohexanecarboxylic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 102274232-amino-4-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-6-quinazolinemethanolHCID 178458058HCID 178458058, compound

Product 1

HCID 22136485N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinazolinyl]-cyclohexanecarboxamideYield 4.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-6-quinazolinemethanol (0.00021 mol), obtained in Example B19, cyclohexanecarboxylic acid (1.2 equiv, 0.000252 mol), N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine, monohydrochloride (1.5 equiv, 0.000315 mol), 1-hydroxy-1H-benzotriazole (1.5 equiv, 0.000315 mol) and triethylamine (1.5 equiv, 0.000315 mol) in THF (2 ml) was stirred at room temperature for 18 hours, then taken up in water. The organic layer was separated and the solvent was evaporated. The residue was purified by HPLC. The product fractions were collected and the solvent was evaporated, yielding 0.006 g (4.8%) of N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinazolinyl]-cyclohexanecarboxamide, MS (ESI) m/z: 586 588 590.

Workup

  1. customThe organic layer was separated
  2. customthe solvent was evaporated
  3. customThe residue was purified by HPLC
  4. customThe product fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-03753b49936d4c87953711ffe6ee3db5
Source dataset
uspto-grants-2006_05
Patent number
US07053105B2

Reaction notes

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