Methyl isothiocyanate → HCID 9958632, compound

HRID 1837386Notes

Reaction equation

HRID 1837386 reaction equation
[CH:1]1([C@@H:7]([NH:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:11])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:35][N:36]=[C:37]=[S:38]>C(Cl)Cl>[CH:1]1([C@@H:7]([NH:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:13]=2[CH2:28][N:29]2[CH2:34][CH2:33][N:32]([C:37](=[S:38])[NH:36][CH3:35])[CH2:31][CH2:30]2)=[O:11])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 9825316HCID 9825316, compound

Product 1

HCID 9958632HCID 9958632, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.4 g (0.87 mmol) of 2-phenyl-3-piperazin-1-ylmethyl-quinoline-4carboxylic acid ((S)-1-cyclohexyl-ethyl)-amide (compound of Example 34) were dissolved in 10 ml of methylene chloride and 0.09 g methylisothiocyanate were added. The mixture was stirred for 5 h at room temperature and the solvent was concentrated in vacuo and the residue was purified by flash chromatography on silicagel (EtOAc/heptane: 95/5) to afford 0.43 g (yield 92%) of the title compound as white crystals.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customthe residue was purified by flash chromatography on silicagel (EtOAc/heptane: 95/5)

Sources & evidence

ORD record
ord-e8dd424bef984d2bb06916590a24fa42
Source dataset
uspto-grants-2004_08
Patent number
US06780875B2

Reaction notes

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