Acetic Acid → HCID 57651757, compound

HRID 1892116Notes

Reaction equation

HRID 1892116 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 (CDCl3) 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-eaabed0b5f00426db4395eaabf9dadfe
Source dataset
uspto-grants-2013_08
Patent number
US08507671B2

Reaction notes

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