Sodium Carbonate → 2-(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl]-1-[4-(5,6-dihydro-4H-(1,3) thiazin-2-yl)-piperazin-1-yl]-ethanone

HRID 239194Notes

Reaction equation

HRID 239194 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]=[C:6]=[S:7].C(=O)([O-])[O-].[Na+].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[N:23]([CH2:33][C:34]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[O:35])[N:22]=2)=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:25]=[C:24]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[N:23]([CH2:33][C:34]([N:36]3[CH2:37][CH2:38][N:39]([C:6]4[S:7][CH2:2][CH2:3][CH2:4][N:5]=4)[CH2:40][CH2:41]3)=[O:35])[N:22]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1377143-Bromopropyl isothiocyanateHCID 866865252-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-piperazin-1-yl-ethanone

Product 1

HCID 866865242-(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl]-1-[4-(5,6-dihydro-4H-(1,3) thiazin-2-yl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

0.08 mL 1-bromo-3-isothiocyanato-propane and 305 mg sodium carbonate were added to 250 mg 2-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-piperazin-1-yl-ethanone in 5 mL chloroform. The reaction was stirred over night at 60° C. The reaction was filtered over silicagel and the solvent was evaporated. The residue was crystallized from diethylether to yield 206 mg of the desired compound. Rt: 1.17 min (method B), (M+H)+: 483

Workup

  1. filtrationThe reaction was filtered over silicagel
  2. customthe solvent was evaporated
  3. customThe residue was crystallized from diethylether

Sources & evidence

ORD record
ord-bc0892879f6944078d57f28edab71814
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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