HCID 54591943, compound → HCID 67453142, compound

HRID 2276760Notes

Reaction equation

HRID 2276760 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][NH:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1>C1COCC1>[NH2:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([NH:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([CH3:20])[CH3:19])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 54591943HCID 54591943, compoundHCID 68718528lithium aluminium hydride THF

Product 1

HCID 67453142HCID 67453142, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL round bottom flask was added 6-(2-(4-fluorophenyl)-2-methylpropylamino)nicotinonitrile (1.0 g, 3.7 mmol, 1.0 equiv) and THF (15 mL), followed by the addition of 1M lithium aluminum hydride/THF (14.8 mL, 14.8 mmol, 4.0 equiv). The reaction was heated to reflux for 3 h and allowed to cool to rt. The reaction mixture was then quenched by the sequential slow addition water (0.6 mL), 3N NaOH (0.6 mL), and water (1.7 mL). The resultant precipitate was filtered and the filtrate was then dried (Na2SO4) and concentrated to give 1.0 g (99%) of 5-(aminomethyl)-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridin-2-amine.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 h
  3. customThe reaction mixture was then quenched by the sequential slow addition water (0.6 mL), 3N NaOH (0.6 mL), and water (1.7 mL)
  4. filtrationThe resultant precipitate was filtered
  5. dry with materialthe filtrate was then dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43dc2703e46a49dea719a651fb6e3df7
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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