Benzoic Acid → HCID 44593639, compound

HRID 2114150Notes

Reaction equation

HRID 2114150 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.[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 44593639HCID 44593639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (42 mg, 0.15 mmol) and benzoic acid (0.40 mmol) were mixed in THF (5 ml). Carbodiimde resin (495 mg, 0.5 mmol) was added and shaking continued for 18 h. The reaction was filtered, the resin washed with THF and methanol and the combined filtrate and washings filtered through an SPE (SCX) to give, after evaporation of the solvent under vacuum, N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)benzamide. NMR; δH [2H6]—DMSO 10.25,(1H, s), 8.62,(1H, t), 7.95-7.92,(4H, m), 7.73,(1H, dd), 7.69,(1H, d), 7.60-7.50,(3H, m), 7.44,(2H, d), 7.28,(1H, d), 3.16,(2H, t), 2.20,(3H, s), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.41 min, MH+385.

Workup

  1. filtrationThe reaction was filtered
  2. washthe resin washed with THF and methanol
  3. filtrationthe combined filtrate and washings filtered through an SPE (SCX)
  4. customto give
  5. customafter evaporation of the solvent under vacuum, N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)benzamide

Sources & evidence

ORD record
ord-fccb5594828d46939ae3ddb1b5ff1d4e
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

Loading…