HCID 11295862, compound → HCID 135499915, compound

HRID 1828077Notes

Reaction equation

HRID 1828077 reaction equation
Cl.C([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[C:17]1[CH:21]=[CH:20][N:19]([CH:22]([O:36][CH2:37][CH3:38])[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[NH:35])[NH2:34])=[CH:29][CH:28]=2)=[O:24])[N:18]=1)C1C=CC=CC=1>C(O)C.[Pd]>[ClH:16].[C:33]([C:30]1[CH:29]=[CH:28][C:27]([CH2:26][NH:25][C:23](=[O:24])[CH:22]([N:19]2[CH:20]=[CH:21][C:17]([C:11]3[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=3[OH:9])=[N:18]2)[O:36][CH2:37][CH3:38])=[CH:32][CH:31]=1)(=[NH:34])[NH2:35]

Participants

4

Reactant 1

HCID 11295862HCID 11295862, compound

Product 1

HCID 135499915HCID 135499915, compoundYield 114.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of 10% Pd/C (10 mg) at r.t. in ethanol (2 ml) was added (RS)-2-[3-(2-benzyloxy-5-chloro-phenyl)-pyrazol-1-yl]-N-(4-carbamimidoyl-benzyl)-2-ethoxy-acetamide hydrochloride (100 mg). Stirring at r.t. under a hydrogen atmosphere was continued for 3 hrs. The catalyst was filtered off over a celite pad and washed with ethanol. The filtrate was concentrated to give (RS)-N-(4-carbamimidoyl-benzyl)-2-[3-(5-chloro-2-hydroxy-phenyl)-pyrazol-1-yl]-2-ethoxy-acetamide hydrochloride (48 mg) as off-white solid. MS 428.2 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered off over a celite pad
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-880acbb95a934939b856e4be07f4245b
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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