Propionic Acid → HCID 44578401, compound

HRID 2114141Notes

Reaction equation

HRID 2114141 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:25])[CH2:23][CH3:24]>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:25])[CH2:23][CH3:24])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 1032Propionic AcidHCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamide

Product 1

HCID 44578401HCID 44578401, 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 propionic acid (18.5 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)propionamide. NMR; δH [2H6]—DMSO 9.84,(1H, s), 8.60,(1H, t), 7.91,(2H, d), 7.50-7.47,(2H, m), 7.40,(2H, d), 7.21,(1H, d), 3.16,(2H, t), 2.29,(2H, q), 2.15,(3H, s), 1.08-1.02,(4H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.00 min, MH+337.

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)propionamide

Sources & evidence

ORD record
ord-9722e32c08214a45bb0ab9f431e983d3
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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