4-Fluorobenzylamine → HCID 58696822, compound

HRID 2211674Notes

Reaction equation

HRID 2211674 reaction equation
F[C:2]1[N:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([O:17][CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[CH3:24])[CH:8]=1)=[O:5].[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CCOC(C)=O>[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:2]2[N:28]=[CH:27][CH:26]=[CH:25][C:3]=2[C:4]([NH:6][C:7]2[CH:12]=[C:11]([C:13]([F:15])([F:14])[F:16])[CH:10]=[C:9]([O:17][CH2:18][C@@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[CH3:24])[CH:8]=2)=[O:5])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 21959664HCID 21959664, compound

Product 1

HCID 58696822HCID 58696822, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

2-Fluoro-N-[3-(1-methyl-pyrrolidin-2-ylmethoxy)-5-trifluoromethyl-phenyl]-nicotinamide (300 mg), TEA (314 μL) and 4-fluorobenzylamine (170 μL) were combined in a sealed tube and heated to 90° C. for 3 h. Cooled to RT and the mixture was diluted with EtOAc, washed with sat. NH4Cl (2×), brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (CH2Cl2/MeOH/NH4OH 95/5/0.5) to provide an off-white foam upon drying. M+H 503. Calc'd for C26H26F4N4O2: 502.20.

Workup

  1. temperatureCooled to RT
  2. washwashed with sat. NH4Cl (2×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (CH2Cl2/MeOH/NH4OH 95/5/0.5)
  7. customto provide an off-white foam
  8. customupon drying

Sources & evidence

ORD record
ord-ed68328fa71c43689990f21a31549647
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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