Triethylamine → 4'-Trifluoromethylbiphenyl-2-carboxylic acid (4-benzyloxy-2-dimethylcarbamoylphenyl)amide

HRID 2114178Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C(N(CC)CC)C.[F:28][C:29]([F:46])([F:45])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[C:37]([C:42](Cl)=[O:43])=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:32][CH:31]=1>C(OCC)(=O)C>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:2]([NH:1][C:42]([C:37]2[C:36]([C:33]3[CH:34]=[CH:35][C:30]([C:29]([F:28])([F:45])[F:46])=[CH:31][CH:32]=3)=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:43])=[C:3]([C:4](=[O:5])[N:6]([CH3:7])[CH3:8])[CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Amino-5-benzyloxy-N,N-dimethylbenzamide (950 mg) was dissolved in ethyl acetate (10 mL), and thereto was added triethylamine (533 mg). The solution was cooled to 0° C. and 4′-trifluoromethylbiphenyl-2-carbonyl chloride (synthesized from 0.934 g of corresponding carboxylic acid) was added. The mixture was stirred overnight at room temperature. After removal of the insoluble materials by filtration, the filtrate was concentrated and purified by column chromatography on silica gel to give 4′-trifluoromethylbiphenyl-2-carboxylic acid (4-benzyloxy-2-dimethylcarbamoylphenyl)amide (1.23 g).

Workup

customAfter removal of the insoluble materials
filtrationby filtration
concentrationthe filtrate was concentrated
custompurified by column chromatography on silica gel

Sources & evidence

ORD record: ord-a97b967e35fa40eeb19401c37e656564
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432392B2

Reaction notes

Loading…