Triethylamine → HCID 178448488, Verbindung

HRID 538781

Reaktionsgleichung

Reaktionsgleichung von HRID 538781
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([F:25])=[C:20]([CH:24]=1)[C:21](Cl)=[O:22].C(N(CC)CC)C>C1COCC1.CCOC(C)=O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:21](=[O:22])[C:20]2[CH:24]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[F:25])/[N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27736045-Chloro-2-fluorobenzoyl chlorideHCID 668515205-tert-Butyl-3-isobutylthiazol-2(3H)-imine

Produkt 1

HCID 178448488HCID 178448488, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-tert-Butyl-3-isobutylthiazol-2(3H)-imine (Example 16A, 1.5 g, 7.1 mmol) was dissolved in 10 mL of THF. 5-Chloro-2-fluorobenzoyl chloride (1.4 g, 7.1 mmol) was added then triethylamine (3 mL, 21.6 mmol) and the mixture stirred at room temperature for 3 hours. The reaction was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography using a gradient from 0 to 40% EtOAc in hexanes afforded the title compound. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 0.98 (d, J=6.74 Hz, 6H) 1.36 (s, 9H) 2.19-2.39 (m, 1H) 4.01 (d, J=7.14 Hz, 2H) 6.63 (s, 1H) 7.05 (dd, J=10.31, 8.72 Hz, 1H) 7.35 (ddd, J=8.73, 3.97, 2.78 Hz, 1H) 8.10 (dd, J=6.74, 2.78 Hz, 1H). MS (DCI/NH3) m/z 369.2 (M+H)+.

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-db1a946bdada43f6b8ba0643c5019f84
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865753B2

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