2-Methyl-5-phenyl-3-furoic acid → HCID 69204557, compound

HRID 2114117Notes

Reaction equation

HRID 2114117 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.[CH3:22][C:23]1[O:24][C:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][C:27]=1[C:28](O)=[O:29]>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:28]([C:27]4[CH:26]=[C:25]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[O:24][C:23]=4[CH3:22])=[O:29])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 7365162-Methyl-5-phenyl-3-furoic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 69204557HCID 69204557, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (53 mg, 0.189 mmol) and 2-methyl-5-phenyl-3-furoic acid (76.4 mg, 0.378 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 dissolved in methanol, filtered through an SCX SPE and the solvent evaporated under vacuum to give N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2-methyl-5-phenyl-3-furamide (24 mg, 28%). NMR; δH CDCl3 7.81,(2H, d), 7.64,(2H, d), 7.55-7.53,(2H, m), 7.45,(1H, s), 7.40-7.37,(4H, m), 7.30-7.25,(2H, m), 6.78,(1H, s), 6.26,(1H, t), 3.33,(2H, t), 2.70,(3H, s), 2.22,(3H, s), 1.07,(1H, m), 0.57,(2H, m), 0.28,(2H, m). LCMS: retention time 3.93 min, MH+465.

Workup

  1. stirringshaking
  2. waitcontinued for 18 h
  3. filtrationThe solution was filtered off
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in methanol
  6. filtrationfiltered through an SCX SPE
  7. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-bfe9c61fa9cb48e1a9dc324a4da23ac1
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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