1,2-Dichloroethane → N'-((2R,3S)-2-(3-chloro-7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoyl)-4-cyanobenzohydrazide

HRID 470911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470911
[Cl:1][C:2]1[C:3]2[C:10]([NH:11][C@H:12]([C@@H:16]([OH:18])[CH3:17])[C:13]([OH:15])=O)=[CH:9][CH:8]=[C:7]([C:19]#[N:20])[C:4]=2[S:5][CH:6]=1.[C:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1)#[N:22].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:10]([NH:11][C@H:12]([C@@H:16]([OH:18])[CH3:17])[C:13]([NH:30][NH:29][C:27](=[O:28])[C:26]3[CH:25]=[CH:24][C:23]([C:21]#[N:22])=[CH:32][CH:31]=3)=[O:15])=[CH:9][CH:8]=[C:7]([C:19]#[N:20])[C:4]=2[S:5][CH:6]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 4567324-CyanobenzohydrazideHCID 68543453(2R,3S)-2-(3-chloro-7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoic acid

Produkt 1

HCID 68546596N'-((2R,3S)-2-(3-chloro-7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoyl)-4-cyanobenzohydrazideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of (2R,3S)-2-(3-chloro-7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoic acid (0.77 g, 2.48 mmol), 4-cyanobenzhydrazide (440 mg, 2.73 mmol). HOBt (369 mg, 2.73 mmol) in THF:DMF (1:1) (40 mL) was added EDC (712 mg, 3.71 mmol) and Et3N (0.53 mL, 3.80 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min and then at room temperature overnight. The reaction was quenched by adding water and extracted with EtOAc (300 mL). The EtOAc extracts were washed with water, brine and dried over Na2SO4. Removal of the solvent and purification of the residue gave the title compound N′-((2R,3S)-2-(3-chloro-7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoyl)-4-cyanobenzohydrazide (0.83 g, 74%). 1H NMR (400 MHz, Acetone-d6, δ in ppm) 9.82 (b, 2H), 8.10 (d, J=8.2 Hz, 2H), 7.94 (d, J=8.2 Hz, 2H), 7.72 (d, J=8.4 Hz, 1H), 7.70 (s, 1H), 7.53 (d, J=6.8 Hz, 1H), 6.64 (d, J=8.4 Hz, 1H), 4.49 (m, 1H), 4.22 (dd, J=2.9, 6.8 Hz, 1H), 1.41 (d, J=6.4 Hz, 3H).

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. customThe reaction was quenched
  4. additionby adding water
  5. extractionextracted with EtOAc (300 mL)
  6. washThe EtOAc extracts were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent and purification of the residue

Quellen und Nachweise

ORD-Eintrag
ord-663a4456af35406396e2fe22de3e0cd5
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629167B2

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