Ethyl 4-piperidinecarboxylate → 6-Chloro-2-[4-(ethoxycarbonyl)-1-piperidinyl]-5-quinolinecarboxylic acid

HRID 2217877Notes

Reaction equation

HRID 2217877 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([OH:14])=[O:13])=[C:7]([Cl:15])[CH:6]=[CH:5][C:4]=2[N:3]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]1>>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[N:3]=[C:2]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:11]=[CH:10][C:9]=2[C:8]=1[C:12]([OH:14])=[O:13]

Participants

3

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 577339932,6-Dichloroquinoline-5-carboxylic acid

Product 1

HCID 688089486-Chloro-2-[4-(ethoxycarbonyl)-1-piperidinyl]-5-quinolinecarboxylic acidYield 75.1%

Procedure

Prepared according to the method of example 30, using 2,6-dichloro-5-quinolinecarboxylic acid (Example 76(b)) (800 mg) and 4-piperidinecarboxylic acid, ethyl ester (2.7 g). Purification (Varian NH2 cartridge using methanol (100 mL) and then 2% acetic acid in methanol (100 mL) as eluant) afforded the title compound as a solid (900 mg).

Workup

  1. customPrepared
  2. customPurification (Varian NH2 cartridge

Sources & evidence

ORD record
ord-3550d3d753574fac9f729982d70be832
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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