4-Fluorobenzylamine → HCID 10211524, compound

HRID 2211668Notes

Reaction equation

HRID 2211668 reaction equation
Cl[C:2]1[N:37]=[CH:36][CH:35]=[CH:34][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[C:9]([O:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:8]=1)=[O:5].[F:38][C:39]1[CH:46]=[CH:45][C:42]([CH2:43][NH2:44])=[CH:41][CH:40]=1>CCOC(C)=O.O>[F:38][C:39]1[CH:46]=[CH:45][C:42]([CH2:43][NH:44][C:2]2[N:37]=[CH:36][CH:35]=[CH:34][C:3]=2[C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[C:9]([O:20][CH2:21][CH:22]3[CH2:26][CH2:25][CH2:24][N:23]3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:8]=2)=[O:5])=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 673264-FluorobenzylamineHCID 21959554HCID 21959554, compound

Product 1

HCID 10211524HCID 10211524, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

2-Chloro-N-[3-(1-Boc-pyrrolidin-2-ylmethoxy)-4-pentafluoroethyl-phenyl]-nicotinamide (442.8 mg) DIEA (351 μL) and 4-fluorobenzylamine (322 μL) were combined in a sealed tube and heated to 130° C. for 3 h. The mixture was diluted with EtOAc and H2O, the layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified with silica gel chromatography (1% MeOH/CH2Cl2) to obtain an off-white solid.

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with silica gel chromatography (1% MeOH/CH2Cl2)
  7. customto obtain an off-white solid

Sources & evidence

ORD record
ord-b3e0e53c336e47839acc81e84f56e458
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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