2-Butanamine, 3,3-dimethyl- → 2-(4-Chlorophenylsulfonyl)-3-(pyridin-3-ylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile

HRID 840205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 840205
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11](=[C:14](SC)[NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:24][CH:25]([NH2:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11](=[C:14]([NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:30][CH:25]([CH3:24])[C:26]([CH3:29])([CH3:28])[CH3:27])[C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 701501772-(4-Chlorophenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)-2-propenenitrile

Produkt 1

HCID 498242302-(4-Chlorophenylsulfonyl)-3-(pyridin-3-ylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrileAusbeute 58 %

Versuchsvorschrift

2-(4-Chloro-phenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)-2-propenenitrile (0.186 g, 0.5 mmol) was stirred in 1,2,2-trimethylpropylamine (1 ml) for 22 h at 100° C. under nitrogen. The reaction mixture was concentrated. The residue was dissolved in DCM, washed with water, dried (sodium sulfate) and concentrated. The crude product was purified by flash chromatography using ethyl acetate as eluent to give 124 mg (58%) of the title compound as a syrup, which could be crystallised from ethyl acetate/heptane 2:1 to give 65 mg (30%). Mp 172-174° C. 1H NMR (300 MHz, CDCl3): δ=0.85 (s, 9H), 0.9 (d, 3H), 3.03 (m, 1H), 7.35 (m, 2H), 7.48 (d, 2H), 7.80 (d, 2H), 8.33 (br s, 1H), 8.5 (br s, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-953a841a09644735a501b6558a568337
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365609B1

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