Tetrahydrofuran → HCID 57418344, compound

HRID 1868130Notes

Reaction equation

HRID 1868130 reaction equation
[CH3:1][C@H:2]1[N:7]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([OH:23])([CH3:22])[C:18]([F:21])([F:20])[F:19])[CH:12]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][N:4]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[C:32]([F:35])([F:34])[F:33])[CH2:3]1.C1COCC1.[BH4-].[Na+]>CO>[NH2:29][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([N:4]2[CH2:5][CH2:6][N:7]([S:8]([C:11]3[CH:12]=[C:13]([C:17]([OH:23])([CH3:22])[C:18]([F:19])([F:20])[F:21])[CH:14]=[CH:15][CH:16]=3)(=[O:10])=[O:9])[C@H:2]([CH3:1])[CH2:3]2)=[C:25]([C:32]([F:33])([F:34])[F:35])[CH:26]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57418324HCID 57418324, compound

Product 1

HCID 57418344HCID 57418344, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a flask containing 4-((3R)-3-methyl-4-{[3-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl]sulfonyl}piperazin-1-yl)-3-(trifluoromethyl)benzonitrile (50 mg, 0.10 mmol) and 2 mL of THF was added CoCl2 (32.5 mg, 0.25 mmol) at 0° C., then NaBH4 (28.4 mg, 0.75 mmol) was added, followed by adding 1 mL of MeOH. The reaction mixture was stirred at 0° C. for 0.5 hr. Reaction was complete as determined by TLC. The reaction mixture was filtered, washed with EtoAc. The filtrate washed with H2O, then washed with sat. brine and dried over Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography to yield 2-[3-({(2R)-4-[4-(aminomethyl)-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)phenyl]-1,1,1-trifluoropropan-2-ol as a white solid. Yield 29%. HRMS: calcd for C22H25F6N3O3S+H+, 526.15936. found (ESI-FTMS, [M+H]1+), 526.15985.

Workup

  1. customReaction
  2. filtrationThe reaction mixture was filtered
  3. washwashed with EtoAc
  4. washThe filtrate washed with H2O
  5. washwashed with sat. brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-3bdf5bdae2314729a39c2b3061375721
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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