4-Pyridinemethanamine → HCID 58874471, compound

HRID 2217930Notes

Reaction equation

HRID 2217930 reaction equation
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>CC#N>[N+:21]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[C:6]([N:8]([CH2:14][C:15]([F:17])([F:18])[F:16])[CH2:9][C:10]([F:11])([F:12])[F:13])=[O:7])([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Product 1

HCID 58874471HCID 58874471, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (120 mg, 0.345 mmol) and 4-(aminomethyl)pyridine (0.070 mL, 0.380 mmoL) were stirred in 3 mL of CH3CN. The solvent was concentrated. The residue was dissolved in EtOAc and washed with saturated NaHCO3, brine and dried over anhydrous Na2SO4. The product was purified by flash chromatography on silica gel using EtOAc as eluent affording the title compound as yellow oil. Yield: 145 mg (79%); 1H NMR (CDCl3) 4.19 (q, J=8.59 Hz, 4H), 4.71 (d, J=6.25 Hz, 2H), 6.69 (d, J=8.79 Hz, 1H), 7.45 (m, 3H), 8.32 (s, 1H), 8.65 (d, J=6.25 Hz, 2H), 8.73 (m, 1H); MS (ESI) 437.24 (MH+).

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with saturated NaHCO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f731dba0c5014ff8b97ca75cd5826ccd
Source dataset
uspto-grants-2008_08
Patent number
US07407968B2

Reaction notes

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