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Pyridine → HCID 68547459, Verbindung

HRID 470901
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 470901
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:11][C@@H:12]([C:16]2[O:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)=[N:19][N:20]=2)[C@@H:13]([OH:15])[CH3:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[C:35]([O:15][C@@H:13]([CH3:14])[C@@H:12]([NH:11][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[C:9]=1[CH3:10])[C:16]1[O:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)=[N:19][N:20]=1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 442008822-Chloro-4-(((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropyl)amino)-3-methylbenzonitrile

Produkt 1

HCID 68547459HCID 68547459, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a 50 mL round bottomed flask was added 2-chloro-4-((1R,2S)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropylamino)-3-methylbenzonitrile (200 mg, 0.508 mmol, pyridine (1 mL, 12.41 mmol) and methylene chloride (15 mL). Benzoyl chloride (0.295 mL, 2.54 mmol) was then added dropwise and the mixture was stirred at room temperature for 17 h. The reaction mixture was then quenched with 10% aq HCl (15 mL) and methylene chloride (30 mL) was added. The phases were partitioned and the aqueous phase extracted with methylene chloride (30 mL) (×2). The combined organics were washed with a saturated solution of sodium hydrogen carbonate, dried (Na2SO4) and concentrated to furnish a yellow oil (0.308 g, 91%). 1H NMR (Acetone d6, 400 MHz) δ 8.21-8.14 (m, 2 H), 8.03 (d, J=9 Hz, 2 H), 7.96 (d, J=9 Hz, 1 H), 7.81 (t, J=8 Hz, 1 H), 7.65-7.59 (m, 2 H), 7.55-7.49 (m, 2 H), 7.01 (d, J=9 Hz, 1 H), 5.94-5.85 (m, 1 H), 5.64 (dd, J=9 and 6 Hz, 1H), 5.48 (dd, J=5 and 8 Hz, 1H), 2.34 (s, 3 H), 1.62 (d, J=6 Hz, 3 H).

Aufarbeitung

  1. customThe reaction mixture was then quenched with 10% aq HCl (15 mL) and methylene chloride (30 mL)
  2. additionwas added
  3. customThe phases were partitioned
  4. extractionthe aqueous phase extracted with methylene chloride (30 mL) (×2)
  5. washThe combined organics were washed with a saturated solution of sodium hydrogen carbonate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-19fdccc6b67441269a991be293eecddb
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629167B2

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