Sec-Butylamine → HCID 58617238, compound

HRID 550361Notes

Reaction equation

HRID 550361 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10]([F:20])=[N:11][C:12]2[C:17]([C:18]=1F)=[CH:16][N:15]=[CH:14][CH:13]=2.[CH:21]([NH2:25])([CH2:23][CH3:24])[CH3:22]>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)C>[CH:21]([NH:25][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[N:15][CH:16]=2)[N:11]=[C:10]([F:20])[C:9]=1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])([CH2:23][CH3:24])[CH3:22]

Participants

6

Reactant 2

HCID 24874Sec-ButylamineHCID 58617241HCID 58617241, compound

Product 1

HCID 58617238HCID 58617238, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Step 1 (0.10 g) was dissolved in DMF (2 ml). Sec-butylamine (0.1 ml) and DMAP (0.001 g) were added and the mixture was stirred in a sealed tube at ambient temperature for 18 hours. The brown reaction mixture was diluted with diethyl ether, washed with brine and dried over sodium sulphate. After evaporation of the solvent the resulting yellow gum was purified by flash column chromatography on silica gel (40-60) in ethyl acetate:hexane 1:3 to give N-sec-butyl-3-(2-chloro-6-fluorophenyl)-2-fluoro-1,6-naphthyridin-4-amine as a dark yellow solid (0.06 g).

Workup

  1. washwashed with brine
  2. dry with materialdried over sodium sulphate
  3. customAfter evaporation of the solvent the resulting yellow gum
  4. customwas purified by flash column chromatography on silica gel (40-60) in ethyl acetate:hexane 1:3

Sources & evidence

ORD record
ord-2ea099799b85462ab21e341ba4dba674
Source dataset
uspto-grants-2011_05
Patent number
US07947679B2

Reaction notes

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