Acetic Acid → HCID 24906105, compound

HRID 1868137Notes

Reaction equation

HRID 1868137 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]([N: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][CH:35]=O.CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH2:34]([N:26]1[CH2:27][CH2:28][N:23]([C:19]2[CH:18]=[C:17]([S:14]([N:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=4[C:30]([F:31])([F:33])[F:32])[CH2:9][C@H:10]3[CH3:29])(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=2)[CH2:24][CH2:25]1)[CH3:35]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 24906147HCID 24906147, compound

Product 1

HCID 24906105HCID 24906105, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-[(3-piperazin-1-ylphenyl)sulfonyl]piperazine (120 mg, 0.247 mmol) in MeOH (2 mL) was added CH3CHO (12 mg, 0.27 mmol), HOAc (17.7 μL, 0.3 mmol) and NaBH3CN (8 mg, 0.125 mmol) at room temperature. The resultant mixture was stirred till disappearance of starting material as monitored by LCMS. The solvent was removed. The crude product was purified by SiO2 column eluted with DCM/MeOH to give the desired product as a light yellow solid (116 mg, 100%). HRMS: calcd for C24H30F4N4O2S+H+, 515.20983. found (ESI-FTMS, [M+H]1+), 515.20891.

Workup

  1. customThe solvent was removed
  2. customThe crude product was purified by SiO2 column
  3. washeluted with DCM/MeOH

Sources & evidence

ORD record
ord-7c227efbc4174091ac1a1e901a9aa39f
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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