3-(Trifluoromethyl)aniline → HCID 58674630, compound

HRID 1994134Notes

Reaction equation

HRID 1994134 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=O)=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[F:23][C:24]([F:33])([F:32])[C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28].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>CN(C=O)C.CCOC(C)=O>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][C:20](=[O:22])[NH:28][C:27]3[CH:29]=[CH:30][CH:31]=[C:25]([C:24]([F:23])([F:32])[F:33])[CH:26]=3)=[CH:16][CH:17]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 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)HCID 58674341HCID 58674341, compound

Product 1

HCID 58674630HCID 58674630, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-({2-[(methylamino)carbonyl]pyridin-4-yl}oxy)phenyl]-propanoic acid (270 mg, 0.90 mmol), 3-(trifluoromethyl)aniline (158 mg, 0.98 mmol), HATU (409 mg, 1.07 mmol), and DIPEA (348 mg, 2.69 mmol) in DMF (5 mL) was stirred at rt for 16 h. The reaction mixture was diluted with EtOAc and washed with 1N HCl and brine. The organic solution was dried over MgSO4, filtered, and concentrated to give A-4 as a white solid (127 mg, 32%). 1H NMR (300 MHz, d6-DMSO) δ: 10.28 (s, 1H), 8.76 (m, 1H), 8.47 (d, 1H), 8.08 (br s, 1H), 7.75 (br d, 1H), 7.53 (t, 1H), 7.31-7.42 (m, 4H), 7.08-7.19 (m, 3H), 2.97 (t, 2H), 2.76 (d, 3H), and 2.71 (d, 2H). LCMS, FA: Rt=1.89 min, [MH+ 444.1].

Workup

  1. washwashed with 1N HCl and brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74ca5190b1dc441491996897dd72b93c
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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