HCID 9923150, compound → HCID 10268135, compound

HRID 990796Notes

Reaction equation

HRID 990796 reaction equation
[C:1]1([C:7]2[C:8]([C:12]3[NH:16][N:15]=[C:14]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:13]=3)=[CH:9][S:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>[Pd].CO.C(O)(=O)C>[CH:1]1([C:7]2[C:8]([C:12]3[NH:16][N:15]=[C:14]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:13]=3)=[CH:9][S:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 9923150HCID 9923150, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10268135HCID 10268135, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Hydrogenation of [5-(4-cyclohex-1-enyl-thiophen-3-yl)-1-H-pyrazol-3-yl]-phenylamine (50 mg, 0.156 mmol) was carried out using 10% palladium on activated carbon (˜20 mg) in methanol (5 mL) and acetic acid (0.5 mL) under a balloon of hydrogen. After stirring for 16 h, the reaction was filtered through Celite. The filtrate was diluted with ether (50 mL), washed with saturated NaHCO3 solution (2×25 mL) and brine (25 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography gave 29 mg (58%) of [5-(4-cyclohexyl-thiophen-3-yl)-1-H-pyrazol-3-yl]-phenylamine as a white solid.

Workup

  1. filtrationthe reaction was filtered through Celite
  2. additionThe filtrate was diluted with ether (50 mL)
  3. washwashed with saturated NaHCO3 solution (2×25 mL) and brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-0710a1bc7a0544ea85dda3ee777f322b
Source dataset
uspto-grants-2002_10
Patent number
US06462069B2

Reaction notes

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