4-Fluorobenzylamine → HCID 9979242, compound

HRID 2299314Notes

Reaction equation

HRID 2299314 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[C:5](=[O:13])[C:4]2[CH:14]=[C:15]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:16][C:3]1=2.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:8]([C:6]2[C:5](=[O:13])[C:4]3[CH:14]=[C:15]([CH2:17][N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[S:16][C:3]=3[N:2]([CH3:1])[CH:7]=2)=[O:9])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 10286664HCID 10286664, compound

Product 1

HCID 9979242HCID 9979242, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylate (0.300 g) from Preparation No. 4 and 4-fluorobenzylamine (1.02 mL) is stirred at 175° C. for 3 h. The reaction mixture is allowed to cool for several minutes and is then diluted with toluene (15 mL). The resulting off-white precipitate is filtered off and recrystallized from acetonitrile then ethanol to yield 0.184 g (50%) of the title compound as a white, crystalline solid.

Workup

  1. customfrom Preparation No
  2. temperatureto cool for several minutes
  3. filtrationThe resulting off-white precipitate is filtered off
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c39564b68fe648eebde44eb84612721a
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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