Triethylamine → N-Quinolin-7-yl-1-(5-trifluoromethylpyrid-2-yl)-piperidine-4-carboxamide

HRID 494271Notes

Reaction equation

HRID 494271 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]2)=[N:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:33][C:34]1[CH:43]=[C:42]2[C:37]([CH:38]=[CH:39][CH:40]=[N:41]2)=[CH:36][CH:35]=1>ClCCCl.CN(C=O)C>[N:41]1[C:42]2[C:37](=[CH:36][CH:35]=[C:34]([NH:33][C:15]([CH:12]3[CH2:11][CH2:10][N:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][N:7]=4)[CH2:14][CH2:13]3)=[O:17])[CH:43]=2)[CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113777-AminoquinolineHCID 65578Oxalyl chlorideHCID 27777881-[5-(Trifluoromethyl)pyridin-2-yl]piperidine-4-carboxylic acid

Product 1

HCID 57682695N-Quinolin-7-yl-1-(5-trifluoromethylpyrid-2-yl)-piperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

1-(5-Trifluoromethylpyrid-2-yl)-piperidine-4-carboxylic acid (D101) (100 mg, 0.36 mmol) was treated with oxalyl chloride (63 ul, 0.72 mmol) and catalytic DMF in 1,2-dichloroethane (3.5 ml) at 60° C. for 0.75 h. On cooling to room temperature the solvent was removed in vacuo and the residue was dissolved in DCM (2 ml). Triethylamine (30 ul, 0.2 mmol) and 7-aminoquinoline (D55) (27 mg, 0.19 mmol) were added and the reaction stirred at room temperature until complete by tlc. The resultant precipitate was collected by filtration to give the title compound as an off-white solid. MS(ES): MH+ 401, M-H+ 399.

Workup

  1. customwas removed in vacuo
  2. dissolutionthe residue was dissolved in DCM (2 ml)
  3. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-86cc5a4a6fbe4ed693c5d38bcc82e024
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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