3,4-Dimethoxyphenylboronic acid → 2-(3-Carbamoyl-5-methylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

HRID 1515557Notes

Reaction equation

HRID 1515557 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].O.[C:26]([OH:30])(=[O:29])[CH:27]=O>C(#N)C.CN(C=O)C>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH:27]([C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:26]([OH:30])=[O:29])[CH:10]=[C:9]([CH3:11])[CH:8]=1)(=[O:6])[NH2:7]

Participants

6

Reactant 3

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrateHCID 539884413-Amino-5-methylbenzamide

Product 1

HCID 594794972-(3-Carbamoyl-5-methylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acidYield 44.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 89C (75 mg, 0.5 mmol), 3,4-dimethoxyphenylboronic acid (91 mg, 0.5 mmol) and glyoxylic acid monohydrate (46 mg, 0.5 mmol) in acetonitrile (1.0 mL) and DMF (0.1 mL) was heated at in a microwave reactor at 100° C. for 10 min. The precipitate formed was collected by filtration. The filtrate was concentrated and the residue was triturated with ethyl acetate and ether. This solid was combined with the original precipitate to give 89D (76 mg, 44%) as an orange solid. 1H NMR (400 MHz, CD3OD) δ ppm 2.26 (s, 3H) 3.81 (s, 3H) 3.82 (s, 3H) 5.09 (s, 1H) 6.70 (s, 1H) 6.92 (d, J=8.4 Hz, 1H) 7.00 (s, 1H) 7.02 (s, 1H) 7.07 (dd, J=8.4, 2.2 Hz, 1H) 7.11 (d, J=1.8 Hz, 1H).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was triturated with ethyl acetate and ether

Sources & evidence

ORD record
ord-23a0d24a20b04c2caea26d4e89a92353
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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