5-(4-Chlorophenyl)-2-furoic acid → HCID 69203690, compound

HRID 2114116Notes

Reaction equation

HRID 2114116 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.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][C:32]([C:34](O)=[O:35])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1>C1COCC1>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][C:32]([C:34]([NH:1][C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]5[CH2:20][CH2:19]5)=[O:15])=[CH:10][CH:9]=4)[C:5]([CH3:21])=[CH:4][CH:3]=3)=[O:35])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7266935-(4-Chlorophenyl)-2-furoic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 69203690HCID 69203690, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (53 mg, 0.189 mmol) and 5-(4-chlorophenyl)-2-furoic acid (84.2 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 5-(4-chlorophenyl)-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-2- furamide (10 mg, 11%). NMR; δH CDCl3 8.07,(1H, b), 7.85,(2H, d), 7.69-7.65,(3H, m), 7.52,(1H, d), 7.44-7.41,(4H, m), 7.31-7.29,(2H, m), 6.98,(1H, b), 6.79,(1H, d), 3.36,(2H, m), 2.25,(3H, s), 1.10,(1H, m), 0.60,(2H, m), 0.31,(2H, m). LCMS: retention time 3.92 min, MH+485.

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-3261f9f4435b47b78d224364bff9c25b
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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