4-Chlorobenzylamine → HCID 9845342, compound

HRID 2299292Notes

Reaction equation

HRID 2299292 reaction equation
[Br:1][C:2]1[S:18][C:5]2[N:6]([CH2:16][CH3:17])[CH:7]=[C:8]([C:11]([O:13]CC)=O)[C:9](=[O:10])[C:4]=2[CH:3]=1.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:18][C:5]2[N:6]([CH2:16][CH3:17])[CH:7]=[C:8]([C:11]([NH:25][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([Cl:19])=[CH:21][CH:22]=3)=[O:13])[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 13217725HCID 13217725, compound

Product 1

HCID 9845342HCID 9845342, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 2-bromo-7-ethyl4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (Eur. J. Med. Chem. 1987, 22, 139) (0.500 g) and 4-chlorobenzylamine (1.84 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 tan solid. This material is recrystallized from acetic acid/water then ethanol to yield 0.379 g (59%) of the title compound as a white, crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-c434086a004547aa8d52a43e45cb2619
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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