Glyoxylic acid, monohydrate → 2-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyano-4-(ethylsulfonyl)phenylcarbamoyloxy)ethyl)phenyl)acetic acid

HRID 735565Notes

Reaction equation

HRID 735565 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15]([O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])#[N:2].[NH2:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[C:36]([N:40]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:35][CH:34]=[CH:33]2.O.[C:56]([OH:60])(=[O:59])[CH:57]=O>>[C:51]([O:50][C:48]([N:40]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])[C:36]1[C:37]2[C:32](=[CH:31][C:30]([NH:29][CH:57]([C:23]3[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][O:17][C:15](=[O:16])[NH:14][C:5]4[CH:6]=[CH:7][C:8]([S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[C:3]([C:1]#[N:2])[CH:4]=4)=[CH:21][CH:22]=3)[C:56]([OH:60])=[O:59])=[CH:39][CH:38]=2)[CH:33]=[CH:34][N:35]=1)=[O:49])([CH3:54])([CH3:53])[CH3:52]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 68818426HCID 68818426, compound

Product 1

HCID 578426012-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyano-4-(ethylsulfonyl)phenylcarbamoyloxy)ethyl)phenyl)acetic acidYield 86%

Procedure

Using a procedure analogous to that used to prepare 2D, 26B (225 mg, 0.57 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 26C (374 mg, 86%) as a yellow solid. MS (ESI) m/z 773.86 (M+H)+.

Sources & evidence

ORD record
ord-8b4db08dc1f541dab0fda78853a1e6a5
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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