Methyl 3-amino-2-thiophenecarboxylate → HCID 58556932, compound

HRID 469494Notes

Reaction equation

HRID 469494 reaction equation
O.O=[CH:3][C:4]([OH:6])=[O:5].[NH2:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:17][O:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C(#N)C>[CH3:16][O:15][C:13]([C:9]1[S:10][CH:11]=[CH:12][C:8]=1[NH:7][CH:3]([C:22]1[CH:23]=[N:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)[C:4]([OH:6])=[O:5])=[O:14]

Participants

5

Reactant 3

HCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58556932HCID 58556932, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-oxoacetic acid hydrate (156 mg, 1.70 mmol) and methyl 3-aminothiophene-2-carboxylate (267 mg, 1.70 mmol) in acetonitrile (15 ml), was added 6-methoxypyridin-3-ylboronic acid (260 mg, 1.70 mmol). The reaction mixture was refluxed for 2 hours and the solvent was evaporated to obtain 2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-(6-methoxypyridin-3-yl)acetic acid (548 mg, 100% yield). The product was used in the next step without any further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8fd2d2e0b8be4a37956c1540e8241e31
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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