Sec-Butylamine → HCID 58617235, compound

HRID 550360Notes

Reaction equation

HRID 550360 reaction equation
Cl[C:2]1[C:11]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:10]([Cl:20])[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.[CH:21]([NH2:25])([CH2:23][CH3:24])[CH3:22]>CN(C=O)C>[CH:21]([NH:25][C:2]1[C:11]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:10]([Cl:20])[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1)([CH2:23][CH3:24])[CH3:22]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 58617247HCID 58617247, compound

Product 1

HCID 58617235HCID 58617235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The product from Step 3 (0.10 g) was dissolved in DMF (2 ml). Sec-butylamine (0.2 ml) was added and the mixture was refluxed in a sealed tube at 70° C. for 14 hours. The dark coloured reaction mixture was evaporated to give an oil, which was purified by flash column chromatography on silica gel (40-60) in ethyl acetate:hexane 1:1 to give N-sec-butyl-4-chloro-3-(2-chloro-6-fluorophenyl)-1,6-naphthyridin-2-amine as a light yellow gum (0.08 g).

Workup

  1. customreaction mixture
  2. customwas evaporated
  3. customto give an oil, which
  4. customwas purified by flash column chromatography on silica gel (40-60) in ethyl acetate:hexane 1:1

Sources & evidence

ORD record
ord-7ea08ef6c3024b07ba33eb3ee9294375
Source dataset
uspto-grants-2011_05
Patent number
US07947679B2

Reaction notes

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