Ammonia → HCID 22277353, compound

HRID 18160Notes

Reaction equation

HRID 18160 reaction equation
C([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)#N.N.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[N:13]1([C:3]2[O:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[CH:7]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 4837PiperazineHCID 389502-Benzofurancarbonitrile

Product 1

HCID 22277353HCID 22277353, compound

Procedure

In step 1 of Scheme C, bromophenol n undergoes iodination to form bromo-iodo-phenol o. Phenol compound o is then reacted with cinnamoyl halide p in step 2 to afford phenoxy ester compound g. Compound g undergoes a cyclization in step 3 to form benzofuran compound r. In step 4 compound r is reacted with dimethyl formamide in the presence of phosphorus oxychloride to afford benzofuran-2-carboxaldehyde s. Aldehyde compound s is converted to cyano-benzofuran compound t in step 5 by reaction with aqueous ammonia. In step 6 a Buchwald reaction is carried out by reacting compound t with piperazine compound f to afford piperazinyl benzofuran u. The nitrile group of compound u undergoes oxidation in step 7 to give benzofuran carboxamide compound v. Compound v is then deprotected in step 8 to afford compound w, which is a compound of formula II in accordance with the invention.

Workup

  1. customIn step 6 a Buchwald reaction

Sources & evidence

ORD record
ord-5e9d0280915d4f17a5124ce9f1d8cdd3
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

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