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

HRID 2055210Notes

Reaction equation

HRID 2055210 reaction equation
C([O:8][N:9]([CH2:12][C:13]1([C:19]([NH:21][NH:22][C:23]2[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=2)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[O:11])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][N:9]([CH2:12][C:13]1([C:19]([NH:21][NH:22][C:23]2[N:28]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:26]=[CH:25][N:24]=2)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 86606473N-Benzyloxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide

Product 1

HCID 11210627N-Hydroxy-N-{1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamideYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-benzyloxy-N-{1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclohexylmethyl}-formamide (0.066 g, 0.15 mmol) in ethanol (5 mL) was added 10% Pd/C (0.03 g). The reaction mixture was subjected to hydrogenation for 3 h at room temperature. The reaction mixture was then filtered through a pad of Celite@, and washed with ethanol (20 mL). Removal of the solvent provided the title compound as a white solid (0.045 g, 85%). MH+362.

Workup

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

Sources & evidence

ORD record
ord-a31f773860984d1d8d97d92448222e7c
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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