Glyoxylic acid, monohydrate → 2-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(4-(3-cyanophenylamino)-4-oxobutyl)-3-methylphenyl)acetic acid

HRID 735641Notes

Reaction equation

HRID 735641 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:24])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][C:15]=2[CH3:23])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([N:36]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[N:31][CH:30]=[CH:29]2.O.[C:52]([OH:56])(=[O:55])[CH:53]=O>>[C:47]([O:46][C:44]([N:36]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[C:32]1[C:33]2[C:28](=[CH:27][C:26]([NH:25][CH:53]([C:17]3[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][CH2:11][C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=4)=[O:24])=[C:15]([CH3:23])[CH:16]=3)[C:52]([OH:56])=[O:55])=[CH:35][CH:34]=2)[CH:29]=[CH:30][N:31]=1)=[O:45])([CH3:50])([CH3:49])[CH3:48]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 578428184-(4-(3-Cyanophenylamino)-4-oxobutyl)-3-methylphenylboronic acidHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578425742-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(4-(3-cyanophenylamino)-4-oxobutyl)-3-methylphenyl)acetic acidYield 46%

Procedure

Using a procedure analogous to that used to prepare 2D, 55D (200 mg, 0.623 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 55E (200 mg, 46%) as an oil. MS (ESI) m/z 694.4 (M+H)+.

Sources & evidence

ORD record
ord-01cff2f0e9dc421c9b58a81052c800c5
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…