Sodium hydride → HCID 66745584, compound

HRID 2099133Notes

Reaction equation

HRID 2099133 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[H-].[Na+].[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14](F)[C:11]=1[C:12]#[N:13]>O1CCOCC1>[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([O:4][CH2:3][C@@H:2]([NH2:1])[CH2:5][CH3:6])[C:11]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1200842-Amino-1-butanol, (+)-HCID 5226592-Amino-6-fluorobenzonitrile

Product 1

HCID 66745584HCID 66745584, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.01 g (51.3 mmol) (S)-2-amino-1-butanol are dissolved in 30 mL 1,4-dioxane, combined with 2.10 g (52.5 mmol) sodium hydride and stirred for 30 min at ambient temperature. To this reaction mixture are added 5.00 g (36.7 mmol) 2-amino-6-fluorobenzonitrile and the mixture is stirred for 24 h at 50° C. Then the solvent is eliminated in vacuo and the crude product is purified by chromatography. The carrier material used is silica gel and the eluant is dichloromethane to which 5% of a mixture of 90% methanol and 10% saturated aqueous ammonia solution have been added.

Workup

  1. stirringthe mixture is stirred for 24 h at 50° C
  2. customthe crude product is purified by chromatography
  3. additionhave been added

Sources & evidence

ORD record
ord-0016b115574940089be250823c2153d9
Source dataset
uspto-grants-2009_08
Patent number
US07569561B2

Reaction notes

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