N-Benzyloxy-N-{3-butyl-1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-formamide → N-{3-Butyl-1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-N-hydroxy-formamide

HRID 2055214Notes

Reaction equation

HRID 2055214 reaction equation
C([O:8][N:9]([CH2:12][C:13]1([C:21]([NH:23][NH:24][C:25]2[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=2)=[O:22])[CH2:16][CH:15]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14]1)[CH:10]=[O:11])C1C=CC=CC=1>CO.[Pd]>[CH2:17]([CH:15]1[CH2:16][C:13]([CH2:12][N:9]([OH:8])[CH:10]=[O:11])([C:21]([NH:23][NH:24][C:25]2[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=2)=[O:22])[CH2:14]1)[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 1

HCID 86606489N-Benzyloxy-N-{3-butyl-1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-formamide

Product 1

HCID 86606493N-{3-Butyl-1-[N'-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-N-hydroxy-formamideYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxy-N-{3-butyl-1-[N′-(4-trifluoromethyl-pyrimidin-2-yl)-hydrazinocarbonyl]-cyclobutylmethyl}-formamide (0.07 g, 0.15 mmol) in methanol (10 mL) was added 10% Pd/C (0.02 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 beige solid (0.042 g, 73%). MH+390.

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-873d8cb4679e4969922a619533a0795b
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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