3-(Trifluoromethyl)aniline → HCID 53345203, compound

HRID 1464978Notes

Reaction equation

HRID 1464978 reaction equation
[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8](/[CH:11]=[CH:12]/[C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=O)[C:4]=2[N:5]=[CH:6][N:7]=1.[F:23][C:24]([F:33])([F:32])[C:25]1[CH:26]=[C:27]([NH2:31])[CH:28]=[CH:29][CH:30]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8](/[CH:11]=[CH:12]/[C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([NH:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:32])[F:33])[CH:26]=3)=[O:18])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67359144HCID 67359144, compound

Product 1

HCID 53345203HCID 53345203, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-3-(2-(4-aminothieno[3,2-d]pyrimidine-7-yl)vinyl)-4-methylbenzoic acid (30 mg, 0.096 mmol) was dissolved in DMF (1 mL), 3-(trifluoromethyl)benzeneamine (16 mg, 0.096 mmol), HATU (110 mg, 0.289 mmol) and TEA (67 μL, 0.48 mmol) was added thereto and stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried with MgSO4, filtered and concentrated. The resulting mixture was purified by silica gel chromatography to obtain the title compound (36 mg, 82% yield).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6cc3099f0eec4b5cbd99c373f3c1fb48
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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