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Methyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylate → Methyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylate

HRID 1425275
Notes
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Reaction equation

HRID 1425275 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:20]=3[N:19]=2)[CH2:14][C@H:13]1[O:31][CH3:32])=O)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:20]=3[N:19]=2)[CH2:14][C@H:13]1[O:31][CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 86648757Methyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86648756Methyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst
HCID 702
Ethanol
Solvent

Procedure

Methyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-1H-benzimidazole-4-carboxylate obtained in Example (187b) (330 mg) was dissolved in ethanol (15 mL). A 10% palladium-carbon catalyst (160 mg) was added, and the mixture was stirred in a hydrogen atmosphere throughout the day. The reaction solution was filtered through celite and then concentrated under reduced pressure to obtain 220 mg of the title compound as a colorless oily substance. The resulting compound was used for the next reaction without purification.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c80ce3fce10468ca60c74f14aea1eea
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927588B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes