Triethylamine → HCID 23537265, compound

HRID 1792508Notes

Reaction equation

HRID 1792508 reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[C:20]2[N:27]1[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=O)[CH2:29][CH2:28]1.[F:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1>O1CCCC1.O>[F:36][C:37]1[CH:43]=[CH:42][C:40]([NH:41][C:33]([CH:30]2[CH2:29][CH2:28][N:27]([C:20]3[C:19]4[C:24](=[CH:25][CH:26]=[C:17]([Br:16])[CH:18]=4)[N:23]=[CH:22][CH:21]=3)[CH2:32][CH2:31]2)=[O:35])=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 62365Isobutyl chloroformateHCID 220311281-(6-Bromo-4-quinolyl)-4-piperidinecarboxylic acid

Product 1

HCID 23537265HCID 23537265, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.34 mL triethylamine and 0.13 mL isobutyl chloroformate were added to a solution of 50 mg 1-(6-bromo-4-quinolyl)-4-piperidinecarboxylic acid in tetrahydrofuran (5 mL) with stirring under ice-cooling, and the mixture was stirred for 0.5 hour in a stream of nitrogen. To this solution was added a solution of 1.5 mL 4-fluoroaniline in tetrahydrofuran (8 mL), and the mixture was stirred at 60° C. for 2 hours. Water was added to the reaction mixture which was then extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 73 mg of the title compound as pale purple crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 0.5 hour in a stream of nitrogen
  3. stirringthe mixture was stirred at 60° C. for 2 hours
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. custompurified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7db04d89c66a42aab25295c376d9c7a8
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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