Ethanol → HCID 46200206, compound

HRID 1930694Notes

Reaction equation

HRID 1930694 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH:11]2[CH2:16][CH:15]([C:17]([F:20])([F:19])[F:18])[CH2:14][CH2:13][C:12]2=O)=O)=[CH:4][CH:3]=1.[CH3:22][C:23]1[N:24]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH2:37])=[NH:36])=[CH:30][CH:29]=2)[CH:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+].CCO>O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:11]3[CH2:16][CH:15]([C:17]([F:20])([F:19])[F:18])[CH2:14][CH2:13][C:12]=3[N:36]=[C:35]([NH:34][C:31]3[CH:32]=[CH:33][C:28]([N:24]4[CH:25]=[CH:26][N:27]=[C:23]4[CH3:22])=[CH:29][CH:30]=3)[N:37]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 59333749HCID 59333749, compoundHCID 178432900HCID 178432900, compound

Product 1

HCID 46200206HCID 46200206, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

2-(2-(4-Fluorophenyl)acetyl)-4-(trifluoromethyl)cyclohexanone (75 mg, 0.25 mmol), 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine (53.4 mg, 0.25 mmol) and potassium carbonate (68.6 mg, 0.50 mmol) were added to a microwave vial. EtOH (3 mL) was added and the reaction was heated to 130° C. for 2 h. DCM (3 mL) and water (3 mL) were added. The organic phase was separated and the solvent was evaporated. The product was purified by preparative HPLC yielding 4-(4-fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-6-(trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-2-amine (30.0 mg, 25.1%).

Workup

  1. customThe organic phase was separated
  2. customthe solvent was evaporated
  3. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-d3e24dd7aaa5428c89e558632bf6bf00
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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