tert-butyl 2-(2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)-N-(3-nitrobenzyl)acetamido)acetate → tert-butyl 2-(N-(3-aminobenzyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetamido)acetate

HRID 735632Notes

Reaction equation

HRID 735632 reaction equation
[C:1]([O:5][C:6]([N:8]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:42]3[CH:47]=[C:46]([CH3:48])[C:45]([CH2:49][CH2:50][OH:51])=[C:44]([CH3:52])[CH:43]=3)[C:21]([N:23]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[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]>CO.[Pd]>[NH2:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:23]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[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:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[N:10][CH:11]=[CH:12]2)[C:42]1[CH:47]=[C:46]([CH3:48])[C:45]([CH2:49][CH2:50][OH:51])=[C:44]([CH3:52])[CH:43]=1

Participants

4

Reactant 1

HCID 57842583tert-butyl 2-(2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)-N-(3-nitrobenzyl)acetamido)acetate

Product 1

HCID 57842746tert-butyl 2-(N-(3-aminobenzyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxyethyl)-3,5-dimethylphenyl)acetamido)acetateYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 52D (230 mg, 0.28 mmol) in MeOH (5 mL) with Pd/C (15 mg) was stirred under H2 (60 psi) for 3 h. The reaction mixture was filtered through Celite and concentrated in vacuo to afford 52E (200 mg, 90%) as a yellow solid. MS (ESI) m/z 784.85 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eceb0aab52ed41fd85e5a395838da137
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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