Acetic Acid → HCID 57418371, compound

HRID 1868141Notes

Reaction equation

HRID 1868141 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:29])[CH2:9]2)=[C:4]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.[CH3:34]C(O)=O.[BH3-]C#N.[Na+]>CO.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]4[CH2:28][CH2:27][N:26]([CH3:34])[CH2:25][CH2:24]4)[CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:29])[CH2:9]2)=[C:4]([C:30]([F:33])([F:31])[F:32])[CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 57418370HCID 57418370, compound

Product 1

HCID 57418371HCID 57418371, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-[(3-piperidin-4-ylphenyl)sulfonyl]piperazine (81 mg, 0.155 mmol) in MeOH (2 mL) was added (CHO)n 27 mg, 0.93 mmol), HOAc (13.7 μL, 0.23 mmol) and NaBH3CN (6 mg, 0.093 mmol). The reaction mixture was stirred at room temperature overnight then 50° C. till disappearance of starting material. The reaction was diluted with DCM and quenched with aq. NaHCO3. The organic layer was separated and dried over Na2SO4 and purified on SiO2 gel column eluted with hexanes/EtOAc to give the desired product as a sticky oil (65 mg, 84%). It was redissolved in Et2O and acidified with 1N HCl in Et2O and triturated with hexanes/Et2O to give the titled compound as a white solid. HRMS: calcd for C24H29F4N3O2S+H+, 500.19893. found (ESI-FTMS, [M+H]1+), 500.19765.

Workup

  1. custom50° C.
  2. customquenched with aq. NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. custompurified on SiO2 gel column
  6. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-f6163eaa85d740b8b0cf6d5b6fb92d60
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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