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 1882499Notes

Reaction equation

HRID 1882499 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-c6d93275b4a44412b5d833762fee81b2
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

Loading…