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

HRID 735669Notes

Reaction equation

HRID 735669 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[O:24][CH2:25][CH3:26])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([N:38]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[N:33][CH:32]=[CH:31]2.O.[C:54]([OH:58])(=[O:57])[CH:55]=O>>[C:49]([O:48][C:46]([N:38]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[C:34]1[C:35]2[C:30](=[CH:29][C:28]([NH:27][CH:55]([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]([O:24][CH2:25][CH3:26])[CH:17]=3)[C:54]([OH:58])=[O:57])=[CH:37][CH:36]=2)[CH:31]=[CH:32][N:33]=1)=[O:47])([CH3:52])([CH3:51])[CH3:50]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 68815689HCID 68815689, compound

Product 1

HCID 578426412-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3-ethoxyphenyl)acetic acidYield 64%

Procedure

Using a procedure analogous to that used to prepare 2D, 62G (250 mg, 0.0706 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 63A (329 mg, 64%) as a solid. MS (ESI) m/z 726.4 (M+H)+.

Sources & evidence

ORD record
ord-b28888c328ab4d43b61ffb213e5770e1
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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