Triethylamine → Methyl 1-{[(4'-chloro-4-methylbiphenyl-3-yl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

HRID 922129Notes

Reaction equation

HRID 922129 reaction equation
[NH2:1][C:2]1([C:14]([O:16][CH3:17])=[O:15])[CH2:7][CH2:6][C:5]([O:12][CH3:13])([C:8]([F:11])([F:10])[F:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([CH2:39][C:40](Cl)=[O:41])[CH:33]=2)=[CH:28][CH:27]=1>ClCCl>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([CH2:39][C:40]([NH:1][C:2]3([C:14]([O:16][CH3:17])=[O:15])[CH2:3][CH2:4][C:5]([O:12][CH3:13])([C:8]([F:11])([F:10])[F:9])[CH2:6][CH2:7]3)=[O:41])[CH:33]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23390525(4'-Chloro-4-methylbiphenyl-3-yl)acetyl chlorideHCID 71246475Methyl 1-amino-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

Product 1

HCID 71246665Methyl 1-{[(4'-chloro-4-methylbiphenyl-3-yl)acetyl]amino}-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3.94 g (15.44 mmol) of methyl 1-amino-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylate (Example 22A) and 1.56 g (15.44 mmol) of triethylamine were dissolved in 56 ml of dichloromethane. 3.92 g (14.03 mmol) of (4′-chloro-4-methylbiphenyl-3-yl)acetyl chloride (Example 2A), dissolved in 56 ml of dichloromethane, were added dropwise to this solution, and the reaction mixture was stirred at room temperature overnight. For work-up, the mixture was diluted with dichloromethane and the organic phase was washed with aqueous saturated sodium bicarbonate solution and with aqueous 1% strength citric acid. After drying over sodium sulphate, the organic phase was concentrated and the product was dried. This gave 6.81 g (97% of theory) of the title compound as a white powder.

Workup

  1. additionwere added dropwise to this solution
  2. washthe organic phase was washed with aqueous saturated sodium bicarbonate solution and with aqueous 1% strength citric acid
  3. dry with materialAfter drying over sodium sulphate
  4. concentrationthe organic phase was concentrated
  5. customthe product was dried

Sources & evidence

ORD record
ord-769f63e1a8da40ebb559e5aecae7dd44
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

Loading…