HCID 22064710, compound → HCID 22064707, compound

HRID 1828078Notes

Reaction equation

HRID 1828078 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][C:9](=[O:28])[CH:10]([O:25][CH2:26][CH3:27])[N:11]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)=[N:12]2)=[CH:5][CH:4]=1)#[N:2]>C(O)C.[Pd]>[NH2:22][C:18]1[CH:17]=[C:16]([C:13]2[CH:14]=[CH:15][N:11]([CH:10]([O:25][CH2:26][CH3:27])[C:9]([NH:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:30][CH:29]=3)=[O:28])[N:12]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 22064710HCID 22064710, compound

Product 1

HCID 22064707HCID 22064707, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of 10% Pd/C (214 mg) at r.t. in ethanol (4 ml) under an argon atmosphere was added of (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-[3-(3-nitro-phenyl)-pyrazol-1-yl]-acetamide (2.1 g). The mixture was stirred at r.t. under a hydrogen atmosphere for 18 h. The catalyst was filtered over a celite pad and the cake was washed with ethanol. The filtrate was concentrated. The crude product was purified by chromatography (silica gel, gradient cyclohexane=>EtOAc) to give (RS)-2-[3-(3-amino-phenyl)-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (1.0 g) as off-white solid. MS 376.5 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered over a celite pad
  2. washthe cake was washed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by chromatography (silica gel, gradient cyclohexane=>EtOAc)

Sources & evidence

ORD record
ord-6e50403c46f7471a8fbe35d0deccab83
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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