HCID 22064702, compound → HCID 135724450, compound

HRID 1828082Notes

Reaction equation

HRID 1828082 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:19]([CH3:20])=[CH:18][N:17]([CH:21]([O:34][CH2:35][CH3:36])[C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)=[O:23])[N:16]=1)C1C=CC=CC=1>C(O)C.[Pd]>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:22](=[O:23])[CH:21]([O:34][CH2:35][CH3:36])[N:17]2[CH:18]=[C:19]([CH3:20])[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[OH:8])=[N:16]2)=[CH:31][CH:30]=1)#[N:33]

Participants

4

Reactant 1

HCID 22064702HCID 22064702, compound

Product 1

HCID 135724450HCID 135724450, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of (RS)-2-[3-(2-benzyloxy-phenyl)-4-methyl-pyrazol-1-yl]-N-(4-cyano-benzyl)-2-ethoxy-acetamide (1.2 g, example 10.2) at r.t. in ethanol (20 ml) under an argon atmosphere was added 10% Pd/C (60 mg). The mixture was then stirred under a hydrogen atmosphere for 18 h. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated. The crude product was isolated by chromatography (silica gel, gradient cyclohexane=>cyclohexane/EtOAc 2:3) to give (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-[3-(2-hydroxy-phenyl)-4-methyl-pyrazol-1-yl]-acetamide (428 mg) as white solid. MS 389.5 ([M−H]−)

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was isolated by chromatography (silica gel, gradient cyclohexane=>cyclohexane/EtOAc 2:3)

Sources & evidence

ORD record
ord-3fb5fb12e9ba4f77bfb9aa17c7ca5109
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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