4-(N-Boc-amino)piperidine → [1-(3,4,5,6-Tetrahydro-2H-[1,2']bipyridinyl-4-ylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 2382346Notes

Reaction equation

HRID 2382346 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].[N:15]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:20][CH2:19][CH:18]([NH:21][C:22](N2C=CN=C2)=[O:23])[CH2:17][CH2:16]1>C(O)(C)C.C(Cl)Cl>[C:2]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:22](=[O:23])[NH:21][CH:18]2[CH2:19][CH2:20][N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[CH2:16][CH2:17]2)[CH2:13][CH2:14]1)([CH3:1])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 7238334-(N-Boc-amino)piperidineHCID 21978278N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-1-carboxamide

Product 1

HCID 66630046[1-(3,4,5,6-Tetrahydro-2H-[1,2']bipyridinyl-4-ylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-N-Boc-amino-piperidine (0.396 g, 1.85 mmol) in iso-propanol (5 ml) is added imidazole-1-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-amide (50 ml of a 10 mg/ml solution in DCM, 1.85 mmol) and the reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and recrystallisation of the solid from methanol yields the title product.

Workup

  1. customThe solvent is removed in vacuo and recrystallisation of the solid from methanol

Sources & evidence

ORD record
ord-d186afd00009444ca306153b6c47d7cc
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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