Acetic Acid → HCID 57651757, compound

HRID 907424Notes

Reaction equation

HRID 907424 reaction equation
[N+](C1C=CC([N:10]([C:14]2[C:19]([F:20])=[C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:17]=[C:16]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:15]=2)[C:11](=O)[O-:12])=CC=1)([O-])=O.[CH3:33][NH:34][C:35]1[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=1.C(O)(=O)C>C1COCC1>[F:20][C:19]1[C:14]([NH:10][C:11](=[O:12])[N:34]([CH3:33])[C:35]2[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=2)=[N:15][C:16]([O:27][CH2:28][C:29]([F:30])([F:32])[F:31])=[CH:17][C:18]=1[O:21][CH2:22][C:23]([F:25])([F:24])[F:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 86629200HCID 86629200, compound

Product 1

HCID 57651757HCID 57651757, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrophenyl-3-fluoro-4,6-bis(2,2,2-trifluoroethoxy)pyridin-2-ylcarbamate (520 mg, 1.1 mmol) was dissolved in anhydrous THF (3 mL). To this solution was added N-methyl-4-bromoaniline (200 mg, 1.1 mmol). The reaction was allowed to stir for 12 d. The THF was evaporated and the crude material purified by reverse phase chromatography (HPLC grade CH3CN and H2O, both with 0.1% acetic acid) to afford the product as a tan solid (275 mg, 48% yield): mp 89-90° C.; 1H NMR (CDCl13) δ 8.78 (s, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.29 (d, J=8.8 Hz, 2H), 6.79 (d, J=4.7 Hz, 1H), 5.04-4.95 (q, J=8.8 Hz, 2H), 4.94-4.85 (q, J=9.1 Hz, 2H), 3.27 (s, 3H); ESI/MS 520, 522 (M+H), 518, 520 (M−H).

Workup

  1. customThe THF was evaporated
  2. customthe crude material purified by reverse phase chromatography (HPLC grade CH3CN and H2O

Sources & evidence

ORD record
ord-183e33b6444f4e93836983d39fa5897f
Source dataset
uspto-grants-2011_09
Patent number
US08013154B2

Reaction notes

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