{1-[4-(Isoquinolin-6-ylamino)-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}-carbamic acid benzyl ester → [4-(1-Amino-propyl)-4-(4-methoxy-phenyl)-cyclohexyl]-isoquinolin-6-yl-amine

HRID 45198Notes

Reaction equation

HRID 45198 reaction equation
C(OC(=O)[NH:10][CH:11]([C:14]1([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[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([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[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 67075630{1-[4-(Isoquinolin-6-ylamino)-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}-carbamic acid benzyl ester

Product 1

HCID 67076033[4-(1-Amino-propyl)-4-(4-methoxy-phenyl)-cyclohexyl]-isoquinolin-6-yl-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

48 mg (91.7 μmol) of {1-[4-(Isoquinolin-6-ylamino)-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}-carbamic acid benzyl ester (99) were dissolved in 300 μL of dry methanol and 9.7 μg 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. Rt=0.89 min (Method 19). Detected mass: 390.3 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-53ad4b231bd24174a1ae2f23fdcc6b1f
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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