HCID 67059654, compound → HCID 67059653, compound

HRID 1807737Notes

Reaction equation

HRID 1807737 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])=[N:20][CH:21]=2)=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].C(O)C>[CH2:26]([NH:25][C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])=[CH:21][N:20]=1)=[O:24])[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 1

HCID 67059654HCID 67059654, compound

Product 1

HCID 67059653HCID 67059653, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 23938PalladiumCatalyst

Procedure

1-(5-(4-Benzylpiperazine-1-carbonyl)pyridin-2-yl)-3-butylurea (58 mg, 0.147 mmol) and palladium on carbon 10% (15.61 mg, 0.015 mmol) were stirred in ethanol (2.5 mL containing 3 drops of 5M hydrochoric acid) under a hydrogen atmosphere at 5 bar at room temperature overnight. The mixture was filtered and the residue was taken up in dichloromethane/methanol and loaded on to a strong cation exchange column (2 g) and washed with dichloromethane/methanol. Elution of the column with 2M ammonia in methanol gave the title compound (44 mg).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane/methanol
  3. washElution of the column with 2M ammonia in methanol

Sources & evidence

ORD record
ord-b5d77581ea374f4a89f174a01d1f272d
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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