Butyric Acid → HCID 44578403, compound

HRID 2114142Notes

Reaction equation

HRID 2114142 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:26])[CH2:23][CH2:24][CH3:25]>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:26])[CH2:23][CH2:24][CH3:25])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 264Butyric AcidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 44578403HCID 44578403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (30 mg, 0.11 mmol) and butyric acid (22.0 mg, 0.25 mmol) were mixed in THF (3 ml). Carbodiimde resin (295 mg, 0.31 mmol) was added and shaking continued for 72 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)butyramide. NMR; δH [2H6]—DMSO 9.85,(1H, s), 8.60,(1H, t), 7.91,(2H, d), 7.50-7.49,(2H, m), 7.40,(2H, d), 7.21,(1H, d), 3.16,(2H, t), 2.25,(2H, t), 2.15,(3H, s), 1.59,(2H, m), 1.04,(1H, m), 0.89,(3H, t), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.14 min, MH+351.

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)butyramide

Sources & evidence

ORD record
ord-24b78e8cb7ba4a1b9d52b47cb7045b41
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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