Trifluoroacetic acid → HCID 68582561, compound

HRID 1512251Notes

Reaction equation

HRID 1512251 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.F[C:9]1[N:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].[CH:17]([N:20](C(C)C)[CH2:21]C)(C)[CH3:18]>ClCCl.O1CCCC1>[CH:3]12[CH2:2][CH:17]([N:20]([C:9]3[N:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])[CH2:21]1)[CH2:18][O:5]2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 27832543-Cyano-2-fluoropyridine

Product 1

HCID 68582561HCID 68582561, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
115 °C

Procedure

The product from Example 88B (1.57 g, 7.9 mmol) in dichloromethane (25 mL) was treated with trifluoroacetic acid (5 mL) for 30 min at rt. The reaction mixture was concentrated to dryness. To the residue was added 2-fluoro-nicotinonitrile (1.0 g, 8.19 mmol) and diisopropyl ethylamine (3.2 mL) in tetrahydrofuran (8 mL). The reaction mixture was heated at 115° C. for 10 min under microwave condition. The mixture was concentrated to dryness, and the residue was chromatographed using hexane/ethyl acetate (9:1-6:1) to give the title compound (806 mg, 51%). MS (DCI/NH3) m/z 202 (M+1)+. 1HNMR (400 MHz, CDCl3) δ ppm 1.98 (s, 2H) 3.67 (d, J=10.13 Hz, 1H) 3.91 (dd, J=7.98, 1.53 Hz, 1H) 3.96 (m, 2H) 4.69 (s, 1H) 5.16 (s, 1H) 6.64 (dd, J=7.67, 4.91 Hz, 1H) 7.71 (dd, J=7.36, 1.84 Hz, 1H) 8.26 (dd, J=4.60, 1.84 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. concentrationThe mixture was concentrated to dryness
  3. customthe residue was chromatographed

Sources & evidence

ORD record
ord-032d7065b4854db089e8c579cc3acd0a
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

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