3-Amino-4-methylbenzamide → HCID 59479498, compound

HRID 1515501Notes

Reaction equation

HRID 1515501 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[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:8]=[CH:9][C:10]([CH3:11])=[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:3]=1)(=[O:6])[NH2:7]

Participants

6

Reactant 3

HCID 880433-Amino-4-methylbenzamideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 59479498HCID 59479498, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-amino-4-methylbenzamide (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 (2.0 mL) and DMF (0.2 mL) was heated at 100° C. for 20 min in a microwave reactor. After removal of solvent, the crude was triturated with methylene chloride. The precipitate formed was collected by filtration and washed with methylene chloride to give 5A after drying. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.79 (s, 3H) 3.81 (s, 3H) 5.15 (s, 1H) 6.91 (d, J=8.35 Hz, 1H) 6.95 (s, 1H) 7.05-7.14 (m, 4H); LC-MS 345 (M+H).

Workup

  1. customAfter removal of solvent
  2. customthe crude was triturated with methylene chloride
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with methylene chloride

Sources & evidence

ORD record
ord-36c43f123329452283e05184c643f506
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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