Trifluoroacetic acid → HCID 71494740, compound

HRID 1487014Notes

Reaction equation

HRID 1487014 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1([F:36])[CH2:12][N:11]([C:13](=[O:35])/[CH:14]=[CH:15]\[N:16]2[CH:20]=[N:19][C:18]([C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=3)=[N:17]2)[CH2:10]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1([F:36])[CH2:12][N:11]([C:13](=[O:35])/[CH:14]=[CH:15]\[N:16]2[CH:20]=[N:19][C:18]([C:21]3[CH:22]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=3)=[N:17]2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89404243HCID 89404243, compound

Product 1

HCID 71494740HCID 71494740, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Z)-tert-Butyl(1-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)-3-fluoroazetidin-3-yl)methylcarbamate (0.15 g, 0.279 mmol) was dissolved in DCM (10 mL) and TFA (0.1 mL) was added at 0° C. The reaction mixture was stirred at rt for 4 h and concentrated under reduced pressure to afford 0.5 g of crude product, which was purified by chromatography (0-5% methanol in DCM) to afford 15 mg of (Z)-1-(3-(aminomethyl)-3-fluoroazetidin-1-yl)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)prop-2-en-1-one (Yield 15%). 1H NMR (400 MHz, CDCl3, ppm) δ=9.4 (s, 1H); 8.54 (s, 2H); 8.32 (s, 1H); 8.13 (s, 3H); 7.49-7.46 (d, J=10 Hz, 1H); 6.0-5.97 (d, J=10 Hz, 1H); 4.41-4.06 (m, 4H); 3.49-3.36 (m, 3H). LCMS calcd for C17H15F7N5O [M+H]+ 438.3. found: 438.19 (retention time 2.298 min).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford 0.5 g of crude product, which
  3. customwas purified by chromatography (0-5% methanol in DCM)

Sources & evidence

ORD record
ord-d8930b9235244a2d964eb5b627f3932f
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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