4'-Trifluoromethyl-biphenyl-3-carboxylic acid → HCID 69202928, compound

HRID 2114135Notes

Reaction equation

HRID 2114135 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[F:22][C:23]([F:40])([F:39])[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=2)[C:33](O)=[O:34])=[CH:26][CH:25]=1>C1COCC1>[CH:18]1([CH2:17][NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[C:5]([CH3:21])=[CH:4][CH:3]=[C:2]([NH:1][C:33](=[O:34])[C:32]4[CH:36]=[CH:37][CH:38]=[C:30]([C:27]5[CH:28]=[CH:29][C:24]([C:23]([F:22])([F:39])[F:40])=[CH:25][CH:26]=5)[CH:31]=4)[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 27827184'-Trifluoromethyl-biphenyl-3-carboxylic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 69202928HCID 69202928, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (53 mg, 0.189 mmol) and 3-(4-trifluoromethylphenyl)benzoic acid (151 mg, 0.57 mmol) were mixed in THF (5 ml) and the mixture shaken in a varian tube for 15 min at room temperature. Carbodiimde resin (500 mg) was added and shaking continued for 18 h. The solution was filtered off and concentrated under vacuum. The residue was chromatographed on a silica gel flash column eluting with ethyl acetate/hexane (1:1) and the solvent evaporated under vacuum to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-3-(4-trifluoromethylphenyl)benzamide (67 mg, 67%). NMR; δH CDCl3 8.11,(1H, t), 7.87-7.85,(2H, m), 7.83,(2H, d), 7.77,(1H, m), 7.72,(4H, s), 7.63-7.57,(2H, m), 7.50,(1H, d), 7.41,(2H, d), 7.30,(1H, d), 6.25,(1H, t), 3.34,(2H, m), 2.24,(3H, s), 1.08,(1H, m), 0.57,(2H, m), 0.29,(2H, m). LCMS: retention time 4.01 min, MH+529.

Workup

  1. stirringshaking
  2. waitcontinued for 18 h
  3. filtrationThe solution was filtered off
  4. concentrationconcentrated under vacuum
  5. customThe residue was chromatographed on a silica gel flash column
  6. washeluting with ethyl acetate/hexane (1:1)
  7. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-b5cb26c4924d4cdb96434759f2065f52
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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