HCID 68673875, compound → HCID 59443540, compound

HRID 1927672Notes

Reaction equation

HRID 1927672 reaction equation
[CH:1]1([CH2:7][C:8]2[NH:12][C:11]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[C:22]([C:27]([O:29]CC5C=CC=CC=5)=[O:28])=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][CH:16]=3)=[N:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([CH2:7][C:8]2[NH:12][C:11]([CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[C:22]([C:27]([OH:29])=[O:28])=[N:23][CH:24]=[CH:25][CH:26]=4)=[CH:19][CH:20]=3)=[N:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 68673875HCID 68673875, compound

Product 1

HCID 59443540HCID 59443540, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 3-(4-{2-[5-(cyclohexylmethyl)-1H-imidazole-2-yl]ethyl}phenyl)pyridine-2-carboxylate (70 mg, 0.146 mmol), palladium on carbon (7 mg) and ethanol (3 mL) was stirred under a hydrogen atmosphere for 2 hours. The mixture was filtered, and the filtrate was concentrated to afford 3-(4-{2-[5-(cyclohexylmethyl)-1H-imidazole-2-yl]ethyl}phenyl)pyridine-2-carboxylic acid. LCMS: m/e 390 (M+H)+. 1HNMR (CD3OD, 500 MHz): δ 7.79 (1H, d, J=7.5 Hz), 7.42 (1H, d, J=7.5 Hz), 7.08 (1H, 7.5 Hz), 7.01 (1H, s), 3.11 (2H, t, J=6.0 Hz), 2.97 (2H, t, J=6.5 Hz), 2.45 (2H, d, J=7.5 Hz), 1.65 (4H, m), 1.51 (1H, m), 1.16 (4H, m), 0.90 (2H, m).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-718998123ba14ddd97972b3330871663
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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