2-Amino-N-methylbenzamide → HCID 59516637, compound

HRID 1160439Notes

Reaction equation

HRID 1160439 reaction equation
CO[C:3]1[C:8]([C:9]([C:11](=[C:17](SC)SC)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:7][N:6]=[C:5]([S:22][CH3:23])[N:4]=1.[NH2:24][C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([NH:29][CH3:30])=[O:28]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12]([C:11]1[C:9](=[O:10])[C:8]2[CH:7]=[N:6][C:5]([S:22][CH3:23])=[N:4][C:3]=2[N:24]2[C:17]=1[N:29]([CH3:30])[C:27](=[O:28])[C:26]1[CH:31]=[CH:32][CH:33]=[CH:34][C:25]2=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 3080722-Amino-N-methylbenzamideHCID 58622418HCID 58622418, compound

Product 1

HCID 59516637HCID 59516637, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
140 °C

Procedure

A solution of ethyl 2-(4-methoxy-2-(methylthio)pyrimidine-5-carbonyl)-3,3-bis(methylthio)acrylate (775 mg, 2.069 mmol) and 2-amino-N-methylbenzamide (475 mg, 3.163 mmol) in toluene (5 mL) was heated over stream of nitrogen allowing toluene to evaporate and continued heating as neat at 140° C. for over night. Cooled to rt and precipitate formed from DCM (10 mL) was filtered off. The solvent of mother liquor was removed under reduced pressure and repeated the precipitation process with Et2O (10 mL). Trituration in methanol (10 mL) afforded the desired product as a yellow solid (30 mg, 4 %). MS (m/z): 397 (MH+). 1H NMR (CDCl3) δ: 9.37 (s, 1H), 8.37 (d, 1H), 8.26 (dd, 1H), 7.70 (m, 1H), 7.49 (m, 1H), 4.46 (q, 2H), 3.61 (s, 3H), 2.60 (s, 3H), 1.43 (t, 3H).

Workup

  1. customto evaporate
  2. temperatureCooled to rt
  3. customprecipitate formed from DCM (10 mL)
  4. filtrationwas filtered off
  5. customThe solvent of mother liquor was removed under reduced pressure

Sources & evidence

ORD record
ord-9a7deab2704b4b55a36b3bbdbd8ad936
Source dataset
uspto-grants-2010_10
Patent number
US07816406B2

Reaction notes

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