HCID 76012106, compound → HCID 53328217, compound

HRID 1615404Notes

Reaction equation

HRID 1615404 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]=[CH:31][C:32]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[O:33])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[O:16])[CH2:11][CH2:10]1)=[O:8].[H][H]>C1COCC1.CO.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:10][CH2:11][N:12]([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([N:34]4[CH2:35][CH2:36][O:37][CH2:38][CH2:39]4)=[O:33])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[O:16])[CH2:13][CH2:14]1)=[O:8]

Participants

6

Reactant 2

HCID 76012106HCID 76012106, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53328217HCID 53328217, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 4-((1-methylpyrrol-2-yl)-carbonyl)-N-(1-(4-(3-morpholino-3-oxopropen-1-yl)-phenyl)-piperidin-4-yl)-1-piperazinecarboxamide (100 mg, 0.19 mmol) obtained in Example 11 was dissolved in THF (20 ml) and methanol (5 ml), and 10% Pd—C (39 mg) was added thereto, followed by stirring in a hydrogen atmosphere for 12 hours. After the insoluble material was filtered with Celite, the filtrate was evaporated under reduced pressure, thereby obtaining 4-((1-methylpyrrol-2-yl)-carbonyl)-N-(1-(4-(3-morpholino-3-oxopropyl)-phenyl)-piperidin-4-yl)-1-piperazinecarboxamide (84 mg, 84%) as a white solid.

Workup

  1. filtrationAfter the insoluble material was filtered with Celite
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-80a42a2b681547d2b64d7ef9fc6985da
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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