4-Chlorobenzylamine → HCID 9841188, compound

HRID 2299293Notes

Reaction equation

HRID 2299293 reaction equation
[CH2:1]([N:3]1[CH:8]=[C:7]([C:9]([O:11]CC)=O)[C:6](=[O:14])[C:5]2[CH:15]=[CH:16][S:17][C:4]1=2)[CH3:2].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:9]([C:7]2[C:6](=[O:14])[C:5]3[CH:15]=[CH:16][S:17][C:4]=3[N:3]([CH2:1][CH3:2])[CH:8]=2)=[O:11])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 12428625HCID 12428625, compound

Product 1

HCID 9841188HCID 9841188, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 7-ethyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (Eur. J. Med. Chem. 1987, 22, 139) (0.447 g) and 4-chlorobenzylamine (2.42 mL) is stirred at 190° C. for 1 h. The reaction is then allowed to cool to rt and is diluted with toluene. The resulting precipitate is filtered off and washed with toluene followed by hexanes to yield a pale yellow solid. This material is recrystallized from acetic acid/water then ethanol to yield 0.312 g (45%) of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with toluene
  4. customto yield a pale yellow solid
  5. customThis material is recrystallized from acetic acid/water

Sources & evidence

ORD record
ord-0467ef5b2b6a4905964a292d29b0f37c
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

Loading…