4-Chlorobenzylamine → HCID 178522896, compound

HRID 982701Notes

Reaction equation

HRID 982701 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[CH:13]=[CH:14][S:15][C:3]=12.[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:8]([C:7]2[C:2]([OH:1])=[C:3]3[S:15][CH:14]=[CH:13][C:4]3=[N:5][CH:6]=2)=[O:10])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469639HCID 178469639, compound

Product 1

HCID 178522896HCID 178522896, compound

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 7-hydroxythieno[3,2-b]pyridine-6-carboxylate (223 mg) prepared as described in the literature (Elliott, R. L.; O'Hanlon, P. J.; Rogers, N. H. Tetrahedron 1987, 43, 3295-3302) and 4-chlorobenzylamine (1.2 mL) was heated to 190° C. for 1 h. The crude product was purified by column chromatography (CH2Cl2/methanol, 100/1; 50/1; 33/1) and the resulting solid was recrystallized from glacial acetic acid/water to afford 84 mg of the title compound as a tan solid.

Workup

  1. customprepared
  2. customThe crude product was purified by column chromatography (CH2Cl2/methanol, 100/1; 50/1; 33/1)
  3. customthe resulting solid was recrystallized from glacial acetic acid/water

Sources & evidence

ORD record
ord-c20ccc442a79445cac266f0b9151dfa1
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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