Anthranilamide → HCID 59516535, compound

HRID 1160440Notes

Reaction equation

HRID 1160440 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:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH2:29])=[O:28].[H-].[Na+]>C(Cl)Cl.O>[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[NH:29][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[CH:33][C:25]2=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 6942AnthranilamideHCID 24758Sodium hydrideHCID 58622418HCID 58622418, compound

Product 1

HCID 59516535HCID 59516535, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
140 °C

Procedure

A solution of ethyl 2-(4-methoxy-2-(methylthio)pyrimidine-5-carbonyl)-3,3-bis(methylthio)acrylate (250 mg, 0.668 mmol) and 2-aminobenzamide (118 mg, 0.867 mmol) in DCM (5 mL) was heated over stream of nitrogen allowing DCM to evaporate and continued heating as neat at 140° C. for over night. The residue was dissolved in DMF (7 mL) after cooling to rt and treated with NaH (60 mg, 1.500 mmol). The reaction was stirred at rt for 1 h and diluted with DCM (20 mL) and H2O (20 mL). The layers were separated and DCM was removed under reduced pressure. Trituration of the crude in Et2O (10 mL) afforded the desired product as a yellow solid (50 mg, 20%). MS (m/z): 383 (MH+). 1H NMR (CDCl3) δ: 13.58 (br s, 1H), 9.43 (s, 1H), 8.60 (d, 1H), 8.33 (dd, 1H), 7.79 (m, 1H), 7.59 (m, 1H), 4.48 (q, 2H), 2.62 (s, 3H), 1.46 (t, 3H).

Workup

  1. customto evaporate
  2. dissolutionThe residue was dissolved in DMF (7 mL)
  3. temperatureafter cooling to rt
  4. customThe layers were separated
  5. customDCM was removed under reduced pressure

Sources & evidence

ORD record
ord-a6e8ac79a20b44a1af9d16711e3cc693
Source dataset
uspto-grants-2010_10
Patent number
US07816406B2

Reaction notes

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