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

HRID 735584Notes

Reaction equation

HRID 735584 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][C:21]=2[CH3:29])=[O:16])[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])#[N:2].[NH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37]([N:41]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[N:36][CH:35]=[CH:34]2.O.[C:57]([OH:61])(=[O:60])[CH:58]=O>>[C:52]([O:51][C:49]([N:41]([C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[C:37]1[C:38]2[C:33](=[CH:32][C:31]([NH:30][CH:58]([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)=[C:21]([CH3:29])[CH:22]=3)[C:57]([OH:61])=[O:60])=[CH:40][CH:39]=2)[CH:34]=[CH:35][N:36]=1)=[O:50])([CH3:55])([CH3:54])[CH3:53]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578426384-(2-(3-Cyano-4-(ethylsulfonyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578426262-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyano-4-(ethylsulfonyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)acetic acidYield 44%

Procedure

Using a procedure analogous to that used to prepare 2D, 31B (468 mg, 1.1 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 31C (419 mg, 44%) as a pale yellow solid. MS (ESI) m/z 788.07 (M+H)+.

Sources & evidence

ORD record
ord-52f4d8f180c549e0a4a67fdb71654b00
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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