N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide → N-Hydroxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide

HRID 2055209Notes

Reaction equation

HRID 2055209 reaction equation
C([O:8][N:9]([CH2:12][C:13]1([C:18]([NH:20][NH:21][C:22]2[N:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][N:23]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[O:11])C1C=CC=CC=1>CO.[Pd]>[OH:8][N:9]([CH2:12][C:13]1([C:18]([NH:20][NH:21][C:22]2[N:27]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:25]=[CH:24][N:23]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 86606471N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide

Product 1

HCID 11302437N-Hydroxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamideYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxy-N-{1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclopentylmethyl}-formamide (0.085 g, 0.19 mmol) in methanol (10 mL) was added 10% Pd/C (0.03 g). The reaction mixture was subjected to hydrogenation for 4 h at room temperature. The reaction mixture was then filtered through a pad of Celite@, and washed with methanol (20 mL). Removal of the solvent provided the title compound as a white solid (0.025 g, 38%). MH+348.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite@
  2. washwashed with methanol (20 mL)
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-7beaaaa4429849628236cb6d399b5e45
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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