3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid → HCID 44578805, compound

HRID 2114134Notes

Reaction equation

HRID 2114134 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[N:24]([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])[C:25]([CH3:28])=[CH:26][CH:27]=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:32](=[O:33])[C:31]4[CH:35]=[CH:36][CH:37]=[C:29]([N:24]5[C:25]([CH3:28])=[CH:26][CH:27]=[C:23]5[CH3:22])[CH:30]=4)[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 2133293-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 44578805HCID 44578805, compoundYield 83.1%

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-(2,5-dimethylpyrrol-1-yl)benzoic acid (122 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 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-(2,5-dimethylpyrrol1-yl)benzamide (75 mg, 74%). NMR; δH CDCl3 7.91,(1H, d), 7.83,(2H, d), 7.79,(1H, s), 7.71,(1H, s), 7.61-7.55,(2H, m), 7.49,(1H, s), 7.41,(3H, m), 7.29,(1H, d), 6.24,(1H, m), 5.92,(2H, s), 3.34,(2H, m), 2.23,(3H, s), 2.04,(6H, s), 1.08,(1H, m), 0.57,(2H, m), 0.29,(2H, m). LCMS: retention time 3.80 min, MH+478.

Workup

  1. stirringshaking
  2. waitcontinued for 18 h
  3. filtrationThe solution was filtered off
  4. concentrationconcentrated under vacuum
  5. customThe residue 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-e92a89e0d13843bcba6b14424bcfcdaf
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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