Sodium Carbonate → 1-[3-(4-Chloro-phenyl)-[1,2,4]thiadiazol-5-yl]-4-[2-fluoro-2-(4-methoxy-phenyl)-ethyl]-piperazine

HRID 570571Notes

Reaction equation

HRID 570571 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)O)[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:36])CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([F:36])[C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 711865742-(4-(3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanol

Product 1

HCID 711872281-[3-(4-Chloro-phenyl)-[1,2,4]thiadiazol-5-yl]-4-[2-fluoro-2-(4-methoxy-phenyl)-ethyl]-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-(3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanol (30 mg, 69.6 μmol) and DAST (22.4 mg, 18.4 μl, 139 μmol) in 2 mL DCM at 0-5° C. was warmed to RT and stirred for 2 h. 10% aq. Na2CO3-solution was added and stirred for 10 min. The organic layer was separated and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with a gradient formed from heptane and EtOAc to yield, after evaporation of the product containing fraction, 24 mg (80%) of the title compound as light yellow solid. MS (m/e): 433.3 (MH+).

Workup

  1. stirringstirred for 10 min
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica eluting with a gradient
  5. customformed from heptane and EtOAc
  6. customto yield
  7. customafter evaporation of the product
  8. additioncontaining fraction, 24 mg (80%) of the title compound as light yellow solid

Sources & evidence

ORD record
ord-d9ed4db4b08f4f27b6c935db414da987
Source dataset
uspto-grants-2015_05
Patent number
US09023852B2

Reaction notes

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