4-Fluorobenzylamine → HCID 10184751, compound

HRID 2211670Notes

Reaction equation

HRID 2211670 reaction equation
[CH3:1][C:2]1([CH3:28])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][C:14]=3F)=[CH:8][CH:9]=2)[N:4]([CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH2:3]1.C([O-])(O)=O.[Na+].[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>>[CH3:1][C:2]1([CH3:28])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][C:14]=3[NH:40][CH2:39][C:38]3[CH:41]=[CH:42][C:35]([F:34])=[CH:36][CH:37]=3)=[CH:8][CH:9]=2)[N:4]([CH:21]2[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]2)[CH2:3]1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 516892Sodium BicarbonateHCID 21959461HCID 21959461, compound

Product 1

HCID 10184751HCID 10184751, compound

Conditions

Temperature
85 °C

Procedure

A solution of N-[3,3-dimethyl-1-(1-methyl-piperidin-4-yl)-2,3-dihydro-1H-indol-6-yl]-2-fluoro-nicotinamide (500 mg), 4-fluorobenzylamine (240 μL) and NaHCO3 (359 mg) was dissolved in IpOH (5 mL) and heated to 85° C. overnight. After cooling to RT, the mixture was dried under N2. The residue was partitioned between EtOAc and H2O, the organic layer was separated, washed with brine, dried over Na2SO4 and filtered. Silica was added to the filtrate and concentrated to a residue. It was purified by flash chromatography (10% MeOH/EtOAc) to yield a fluffy yellow solid. M+H 488.4. Calc'd for C29H34FN5O: 487.3.

Workup

  1. temperatureAfter cooling to RT
  2. customthe mixture was dried under N2
  3. customThe residue was partitioned between EtOAc and H2O
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. additionSilica was added to the filtrate
  9. concentrationconcentrated to a residue
  10. customIt was purified by flash chromatography (10% MeOH/EtOAc)
  11. customto yield a fluffy yellow solid

Sources & evidence

ORD record
ord-6401928490cc42baa2d05803deebcd34
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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