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

HRID 735579Notes

Reaction equation

HRID 735579 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][C:16]=2[CH3:24])=[O:11])[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:18]3[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][O:12][C:10](=[O:11])[NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=4)=[C:16]([CH3:24])[CH:17]=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 57842579HCID 57842579, compoundHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 579563672-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3-methylphenyl)acetic acid

Procedure

Using a procedure analogous to that used to prepare 2D, 30D (420 mg, 1.30 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 30E (308 mg) as a tan solid. MS (ESI) m/z 696.15 (M+H)+.

Sources & evidence

ORD record
ord-d01da6e4a42142a7abe1c3d837654c40
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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