3-Aminobenzamide → 2-(3-Carbamoylphenylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3-ethylphenyl)acetic acid

HRID 735644Notes

Reaction equation

HRID 735644 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]([CH:33]=[CH:34][CH:35]=1)[C:30]([NH2:32])=[O:31].O.[C:37]([OH:41])(=[O:40])[CH:38]=O>>[C:30]([C:29]1[CH:28]=[C:27]([NH:26][CH:38]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][O:12][C:10](=[O:11])[NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)=[C:16]([CH2:24][CH3:25])[CH:17]=2)[C:37]([OH:41])=[O:40])[CH:35]=[CH:34][CH:33]=1)(=[O:31])[NH2:32]

Participants

4

Reactant 3

HCID 16453-AminobenzamideHCID 15620607Glyoxylic acid, monohydrateHCID 68818193HCID 68818193, compound

Product 1

HCID 578428562-(3-Carbamoylphenylamino)-2-(4-(2-(3-cyanophenylcarbamoyloxy)ethyl)-3-ethylphenyl)acetic acidYield 72%

Procedure

Using a procedure analogous to that used to prepare 2D, 56B (175 mg, 0.52 mmol) was reacted with 3-aminobenzamide and glyoxylic acid monohydrate to afford 56C (175 mg, 72%) as an oil. MS (ESI) m/z 487.3 (M+H)+.

Sources & evidence

ORD record
ord-814636ecc2804c42bd2bc5f497ce8ca9
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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