HCID 178462796, compound → HCID 178462795, compound

HRID 1645350Notes

Reaction equation

HRID 1645350 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]4[N:35]([CH2:45][CH3:46])[C:36]5[C:41]([CH:42]=4)=[C:40]([O:43][CH3:44])[CH:39]=[CH:38][CH:37]=5)=[O:33])=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH2:45]([N:35]1[C:36]2[C:41](=[C:40]([O:43][CH3:44])[CH:39]=[CH:38][CH:37]=2)[CH:42]=[C:34]1[C:32]([NH:31][C:28]1[CH:29]=[CH:30][C:25]([N:22]2[CH2:23][CH2:24][N:19]([C:17]([C@H:14]3[CH2:13][CH2:12][C@H:11]([C:9]([OH:10])=[O:8])[CH2:16][CH2:15]3)=[O:18])[CH2:20][CH2:21]2)=[N:26][CH:27]=1)=[O:33])[CH3:46]

Participants

4

Reactant 1

HCID 178462796HCID 178462796, compound

Product 1

HCID 178462795HCID 178462795, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-4-(4-{5-[(1-ethyl-4-methoxy-1H-indole-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid benzyl ester (30 mg, 0.05 mmol), 10% Pd/C (50 mg) in methanol (20 mL) was hydrogenated at 50 psi for 2 hr. The solution was filtered and the solvent was removed to afford the product, trans-4-(4-{5-[(1-ethyl-4-methoxy-1H-indole-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carbonyl)-cyclohexane carboxylic acid, as a green solid (10 mg, 40% yield). LCMS for C29H35N5O5 calcd. (m/e) 533, observed 534 (M+H).

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-e71233f2e5c847359b70cd0e54332d50
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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