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

HRID 2055212Notes

Reaction equation

HRID 2055212 reaction equation
C([O:8][N:9]([CH2:12][C:13]1([C:20]([NH:22][NH:23][C:24]2[N:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][N:25]=2)=[O:21])[CH2:19][CH2:18][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:20]([NH:22][NH:23][C:24]2[N:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=[CH:26][N:25]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 86606480N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide

Product 1

HCID 11474305N-Hydroxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamideYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxy-N-{1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cycloheptylmethyl}-formamide (0.11 g, 0.24 mmol) in methanol (10 mL) was added 10% Pd/C (0.03 g). The reaction mixture was subjected to hydrogenation for, 0.25 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 (0.067 g, 75%). MH+376.

Workup

  1. custom0.25 h
  2. customat room temperature
  3. filtrationThe reaction mixture was then filtered through a pad of Celite@
  4. washwashed with methanol (20 mL)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-1a0c8ec6a48846c8872fe834cd6100f8
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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