Glyoxylic acid, monohydrate → 2-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3,5-diethylphenyl)acetic acid

HRID 735609Notes

Reaction equation

HRID 735609 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([O:12][CH2:13][CH2:14][C:15]2[C:20]([CH2:21][CH3:22])=[CH:19][C:18](B(O)O)=[CH:17][C:16]=2[CH2:26][CH3:27])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35]([N:39]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[N:34][CH:33]=[CH:32]2.O.[C:55]([OH:59])(=[O:58])[CH:56]=O>>[C:50]([O:49][C:47]([N:39]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[C:35]1[C:36]2[C:31](=[CH:30][C:29]([NH:28][CH:56]([C:18]3[CH:19]=[C:20]([CH2:21][CH3:22])[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]([CH2:26][CH3:27])[CH:17]=3)[C:55]([OH:59])=[O:58])=[CH:38][CH:37]=2)[CH:32]=[CH:33][N:34]=1)=[O:48])([CH3:53])([CH3:52])[CH3:51]

Participants

4

Reactant 3

HCID 15620607Glyoxylic acid, monohydrateHCID 57842869HCID 57842869, compoundHCID 58717298tert-butyl N-(6-aminoisoquinolin-1-yl)-N-[(tert-butoxy)carbonyl]carbamate

Product 1

HCID 578426492-(1-(Bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3,5-diethylphenyl)acetic acidYield 75%

Procedure

Using a procedure analogous to that used to prepare 2D, 37E (200 mg, 0.55 mmol) was reacted with Intermediate 1 and glyoxylic acid monohydrate to afford 38A (304 mg, 75%) as a yellow oil. MS (ESI) m/z 738.22 (M+H)+.

Sources & evidence

ORD record
ord-3696e51d52d145b88bb8829450c62e10
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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