2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-((R)-1-hydroxypropan-2-yl)phenyl)-N-(3-nitrobenzyl)acetamide → N-(3-aminobenzyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-((R)-1-hydroxypropan-2-yl)phenyl)acetamide

HRID 735699Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[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]([C@@H:40]([CH3:43])[CH2:41][OH:42])=[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].NC1C=C(C=CC=1)CNC(=O)C(NC1C=C2C(=CC=1)C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=NC=C2)C1C=CC(CC(O)CC)=CC=1>>[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:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[N:10][CH:11]=[CH:12]2)[C:34]1[CH:35]=[CH:36][C:37]([C@@H:40]([CH3:43])[CH2:41][OH:42])=[CH:38][CH:39]=1

Participants

Reactant 2

HCID 578426652-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-((R)-1-hydroxypropan-2-yl)phenyl)-N-(3-nitrobenzyl)acetamide

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

Product 1

HCID 57842889N-(3-aminobenzyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-((R)-1-hydroxypropan-2-yl)phenyl)acetamide

Procedure

76H (145 mg, 88%) was obtained from 76G (172 mg, 0.25 mmol) using a procedure similar to that used in the preparation of 70G. MS (ESI) m/z 656.4 (M+H)+.

Sources & evidence

ORD record: ord-0009400aff9d49c99fc956b90d948458
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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