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

HRID 735645Notes

Reaction equation

HRID 735645 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[CH2:24][CH3:25])=[O:11])[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: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]([CH2:24][CH3:25])[CH:17]=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 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 68818193HCID 68818193, compound

Product 1

HCID 688174922-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3-ethylphenyl)acetic acidYield 52%

Procedure

Using a procedure analogous to that used to prepare 2D, 56B (175 mg, 0.52 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 57A (186 mg, 52%) as an oil. MS (ESI) m/z 710.5 (M+H)+.

Sources & evidence

ORD record
ord-fab40245e51845b8ad70088135bee5b8
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…