2,4-Difluoro-1-isothiocyanatobenzene → 1,3-Dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-thiocarboxylic acid (2,4-difluorophenyl)amide

HRID 227263Notes

Reaction equation

HRID 227263 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[S:11].[CH2:12]([N:19]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[NH:22][CH:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:20]1=[O:36])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([N:26]1[CH2:27][CH2:28][C:23]2([N:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:20](=[O:36])[CH:21]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[NH:22]2)[CH2:24][CH2:25]1)=[S:11]

Participants

4

Reactant 2

HCID 5188792,4-Difluoro-1-isothiocyanatobenzeneHCID 688379421,3-Dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

Product 1

HCID 866100641,3-Dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-thiocarboxylic acid (2,4-difluorophenyl)amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,4-Difluorophenyl isothiocyanate (256 mg, 1.50 mmol was added to a solution of 1,3-dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one (503 mg, 1.50 mmol) in toluene (14.3 ml) with stirring under a blanket of nitrogen at RT and the reaction mixture was stirred at 50° C. for 8 h. After removal of the solvent, the desired product 1,3-dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-thiocarboxylic acid (2,4-difluorophenyl)amide was obtained by means of preparative HPLC.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 8 h
  2. customAfter removal of the solvent

Sources & evidence

ORD record
ord-c6bbb4880b904182adf6d896034799b1
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Reaction notes

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