2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-[4-(2-hydroxy-butyl)-phenyl]-N-(3-nitro-benzyl)-acetamide → N-(3-Amino-benzyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-[4-(2-hydroxy-butyl)-phenyl]-acetamide

HRID 735685Notes

Reaction equation

HRID 735685 reaction equation
[C:1]([O:5][C:6]([N:8]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([OH:44])[CH2:42][CH3:43])=[CH:36][CH:35]=3)[C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-])=O)[CH:26]=3)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[NH2:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][NH:23][C:21](=[O:22])[CH:20]([NH:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[C:9]([N:8]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[N:10][CH:11]=[CH:12]2)[C:34]1[CH:35]=[CH:36][C:37]([CH2:40][CH:41]([OH:44])[CH2:42][CH3:43])=[CH:38][CH:39]=1

Participants

3

Reactant 1

HCID 578427912-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-[4-(2-hydroxy-butyl)-phenyl]-N-(3-nitro-benzyl)-acetamide

Product 1

HCID 57842720N-(3-Amino-benzyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-[4-(2-hydroxy-butyl)-phenyl]-acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 70F (110 mg in 10 mL MeOH, 0.16 mmol) was added 10% Pd/C (20 mg). The mixture was hydrogenated at 40 psi for 3 h, then filtered and concentrated to give 70G (107 mg, 100%). MS (ESI) m/z 670.7 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-be52a6a3449246c5a074e23f3bd13548
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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