HCID 67072585, compound → HCID 44599823, compound

HRID 1948174Notes

Reaction equation

HRID 1948174 reaction equation
C(OC(=O)[NH:10][CH:11]([C:14]1([CH3:31])[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)[CH2:16][CH2:15]1)[CH2:12][CH3:13])C1C=CC=CC=1>CO.[Pd]>[NH2:10][CH:11]([C:14]1([CH3:31])[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)[CH2:16][CH2:15]1)[CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 67072585HCID 67072585, compound

Product 1

HCID 44599823HCID 44599823, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

66 mg (153 μmol) of {1-[4-(Isoquinolin-6-ylamino)-1-methyl-cyclohexyl]-propyl}-carbamic acid benzyl ester (80) were dissolved in 500 μL of dry methanol and 5 mg of palladium on activated charcoal (10%) were added. The mixture was stirred under a hydrogen atmosphere until conversion was complete. The catalyst was filtered off and the reaction mixture was evaporated to dryness to give the title compound, which was purified by reversed phase HPLC (water/acetonitrile) to give 30 mg of pure Example 111 as its trifluoroacetic acid salt. Rt=1.02 min (Method L). Detected mass: 298.2 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-7e60000ea26340af9493f9104c0c7cdd
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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