3-(Trifluoromethyl)aniline → HCID 11515898, compound

HRID 1371561Notes

Reaction equation

HRID 1371561 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:12][C:13]([OH:15])=O)[CH2:9][CH2:10][N:11]=2)=[N:4][O:5][N:6]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:12][C:13]([NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=3)=[O:15])[CH2:9][CH2:10][N:11]=2)=[N:4][O:5][N:6]=1

Participants

8

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21071287HCID 21071287, compound

Product 1

HCID 11515898HCID 11515898, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-4,5-dihydroimidazol-1-yl)acetic acid (170 mg, 0.8 mmol) was dissolved in DMF and to this solution 3-trifluoromethyl aniline (1.2 g, 7.4 mmol) was added followed by benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent) (0.44 g, 1.0 mmol) and DIEA (0.4 mL, 2.3 mmol). The reaction mixture was stirred at room temperature overnight and then diluted with saturated sodium bicarbonate and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to an oil which was purified by column chromatography (20–60% ethyl acetate/hexanes) to afford the title compound as a white solid, 35 mg, (0.1 mmol, 12%. 1H NMR (500 MHz, CDCl3) δ 7.83 (s, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.43 (t, J=8.0 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 4.47 (s, 2H), 4.06 (t, J=10.0 Hz, 2H), 3.65 (t, J=10.0 Hz, 2H).

Workup

  1. additionwas added
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated to an oil which
  4. customwas purified by column chromatography (20–60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d2212a62b7bb4ca0bc658e5e19b35dfc
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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