Ethanol → HCID 135430191, compound

HRID 1828081Notes

Reaction equation

HRID 1828081 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:36][CH2:37][CH3:38])[C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[NH:35])[NH:33]O)=[CH:28][CH:27]=2)=[O:23])[N:16]=1)C1C=CC=CC=1.C([OH:41])C>C(O)(=O)C.[Pd]>[C:37]([OH:41])(=[O:36])[CH3:38].[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:22](=[O:23])[CH:21]([O:36][CH2:37][CH3:38])[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)(=[NH:33])[NH2:35]

Participants

5

Reactant 2

HCID 702EthanolHCID 178468075HCID 178468075, compound

Product 1

HCID 135430191HCID 135430191, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalyst

Procedure

To a stirred solution of (RS)-2-[3-(2-benzyloxy-phenyl)-4-methyl-pyrazol-1-yl]-2-ethoxy-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-acetamide (90 mg) at r.t. in ethanol were added acetic acid (3 drops) and 10% Pd/C (9 mg). Stirring at r.t. under a hydrogen atmosphere was continued for 18 hrs. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated. The crude product was purified by chromatography (silica gel, EtOAc/acetone/H2O/HOAc 6:2:1:1) to give (RS)-N-(4-carbamimidoyl-benzyl)-2-ethoxy-2-[3-(2-hydroxy-phenyl)-4-methyl-pyrazol-1-yl]-acetamide acetate (28 mg) as off-white solid. MS 408.5 ([M+H]+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by chromatography (silica gel, EtOAc/acetone/H2O/HOAc 6:2:1:1)

Sources & evidence

ORD record
ord-01b14b7c62ac4bb9b53ffd46f90fbab3
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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