Water → HCID 67253289, compound

HRID 1961520Notes

Reaction equation

HRID 1961520 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]#[N:16])[C:12]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>O1CCOCC1>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[C:13]([C:15]#[N:16])[C:12]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][CH:19]=3)=[N:11]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 67253197HCID 67253197, compound

Product 1

HCID 67253289HCID 67253289, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

1-(4-acetylphenyl)-3-{[4-(methylsulfonyl)phenyl]amino}-1H-pyrazole-4-carbonitrile (30 mg, 0.079 mmol) and sodium borohydride (5.97 mg, 0.158 mmol) were stirred in dioxane (1 mL) at 60° C. overnight. Additional sodium borohydride (5.97 mg, 0.158 mmol) was added and stirring at 60° C. continued for 24 hours. Room temperature was attained, water was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated in DCM to give 1-[4-(1-hydroxyethyl)phenyl]-3-{[4-(methylsulfonyl)phenyl]amino}-1H-pyrazole-4-carbonitrile as a white solid.

Workup

  1. customRoom temperature
  2. extractionthe products extracted into EtOAc (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in DCM

Sources & evidence

ORD record
ord-8947811370b244a69196eb2a0d4246be
Source dataset
uspto-grants-2013_04
Patent number
US08415346B2

Reaction notes

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