Glyoxylic acid, monohydrate → 2-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(3-(3-(3-cyanophenyl)-1-methylureido)propyl)phenyl)acetic acid

HRID 735552Notes

Reaction equation

HRID 735552 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:25])[N:11]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=2)[CH3:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([N:37]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[N:32][CH:31]=[CH:30]2.O.[C:53]([OH:57])(=[O:56])[CH:54]=O>>[C:48]([O:47][C:45]([N:37]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[C:33]1[C:34]2[C:29](=[CH:28][C:27]([NH:26][CH:54]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH2:13][N:11]([CH3:12])[C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=4)=[O:25])=[CH:17][CH:18]=3)[C:53]([OH:57])=[O:56])=[CH:36][CH:35]=2)[CH:30]=[CH:31][N:32]=1)=[O:46])([CH3:51])([CH3:50])[CH3:49]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578427124-(3-(3-(3-Cyanophenyl)-1-methylureido)propyl)phenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578427502-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(3-(3-(3-cyanophenyl)-1-methylureido)propyl)phenyl)acetic acidYield 41%

Procedure

Using a procedure analogous to that used to prepare 2D, 22D (146 mg, 0.43 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 22E (124 mg, 41%) as a yellow solid. MS (ESI) m/z 709.08 (M+H)+.

Sources & evidence

ORD record
ord-413c9d8ae1094f0aaa8ce91d45b0c0b5
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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