Glyoxylic acid, monohydrate → 2-(1-(bis(tert-Butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(4-(3-((tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)phenyl)acetic acid

HRID 735537Notes

Reaction equation

HRID 735537 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([NH:23][C:24](=[O:37])[CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=2)[CH:14]=[CH:15][C:16]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[C:45]([N:49]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[N:44][CH:43]=[CH:42]2.O.[C:65]([OH:69])(=[O:68])[CH:66]=O>>[C:60]([O:59][C:57]([N:49]([C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[C:45]1[C:46]2[C:41](=[CH:40][C:39]([NH:38][CH:66]([C:31]3[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][CH2:25][C:24]([NH:23][C:13]4[CH:14]=[CH:15][C:16]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[C:11]([CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:9])[CH:12]=4)=[O:37])=[CH:29][CH:30]=3)[C:65]([OH:69])=[O:68])=[CH:48][CH:47]=2)[CH:42]=[CH:43][N:44]=1)=[O:58])([CH3:63])([CH3:62])[CH3:61]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578427194-(4-(3-((tert-Butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578427552-(1-(bis(tert-Butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(4-(3-((tert-butoxycarbonyl(methyl)amino)methyl)-4-(isopropylsulfonyl)phenylamino)-4-oxobutyl)phenyl)acetic acid

Procedure

Using a procedure analogous to that used to prepare 2D, 18C (0.151 g, 0.28 mmol) was reacted with Intermediate 1 (0.101 g, 0.28 mmol) and glyoxylic acid monohydrate (0.026 g, 0.28 mmol) to give, after purification by reverse phase HPLC, 18D (168 mg, 66%) as a yellow glass.

Workup

  1. customto give
  2. customafter purification by reverse phase HPLC, 18D (168 mg, 66%) as a yellow glass

Sources & evidence

ORD record
ord-f66eb81b81944c32adb50bedf8a85693
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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