Triethylamine → N-[1-(Cyclohexylmethyl)piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide

HRID 2223884Notes

Reaction equation

HRID 2223884 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34](Cl)=[O:35]>ClCCl>[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=3)[C:34]([C:30]3[O:29][CH:33]=[CH:32][CH:31]=3)=[O:35])[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 230210002-[1-(Cyclohexylmethyl)piperidin-4-ylamino]-5-methylpyridine

Product 1

HCID 9970104N-[1-(Cyclohexylmethyl)piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(cyclohexylmethyl)piperidin-4-ylamino]-5-methylpyridine (216 mg) prepared in Preparation Example 1A-1 and triethylamine (152 mg) in dichloromethane (3 mL) was added 2-furoyl chloride (0.11 mL) dropwise under ice cooling. The solution was stirred at room temperature for 18 hours. Silica gel (NH silica gel) was added to the reaction solution, and it was concentrated under reduced pressure. The resulting residue was purified by chromatography (NH silica gel, hexane:ethyl acetate=2:1) to give the title compound as a colorless crystal (271 mg).

Workup

  1. additionSilica gel (NH silica gel) was added to the reaction solution, and it
  2. concentrationwas concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography (NH silica gel, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-99a8df947bcf419c9a13069ccf15e54d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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