4-Methyl-3-nitrobenzoic acid → HCID 2056375, compound

HRID 1051252Notes

Reaction equation

HRID 1051252 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:47][C:48]([F:57])([F:56])[C:49]1[CH:50]=[C:51]([CH:53]=[CH:54][CH:55]=1)[NH2:52]>C(OCC)(=O)C.CN(C)C=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:52][C:51]2[CH:53]=[CH:54][CH:55]=[C:49]([C:48]([F:47])([F:56])[F:57])[CH:50]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 73194-Methyl-3-nitrobenzoic acidHCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 2056375HCID 2056375, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methyl-3-nitrobenzoic acid (14.6 g, 81.0 mmol) was stirred in a solvent of dimethyl formamide (40 mL). The reaction solution was added with HATU (47.2 g, 124 mmol), DIPEA (32.5 mL, 186 mmol) and 3-(trifluoromethyl)aniline (7.72 mL, 62.1 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated solid was added with ethyl acetate, and stirred for 2 hours or more. The resulting solid was filtered under reduced pressure, and washed with ethyl acetate and methanol. The filtered solid was dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (14.9 g, 74%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrated solid was added with ethyl acetate
  7. stirringstirred for 2 hours or more
  8. filtrationThe resulting solid was filtered under reduced pressure
  9. washwashed with ethyl acetate and methanol
  10. customThe filtered solid was dried
  11. temperaturewith warm wind in an oven (40° C.) for 3 hours or more

Sources & evidence

ORD record
ord-8198d8ffe5e2485d9ef100bab8a1cfcc
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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