Acetyl chloride → (2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

HRID 1675451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1675451
[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][N:24](C(OC(C)(C)C)=O)[C@H:23]([C:33](=[O:42])[N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])[CH2:22]1.C(Cl)(=O)C>CO>[ClH:1].[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][NH:24][C@H:23]([C:33]([N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])=[O:42])[CH2:22]1

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 66650750(2S,4S)-tert-butyl 4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-2-(hex-5-enyl(methyl)carbamoyl)pyrrolidine-1-carboxylate2×

Produkt 1

HCID 66650405(2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Compound 134 (20.37 g) was suspended in anhydrous methanol (120 mL) under argon at room temperature. Separately acetyl chloride (3 eq.) was added to anhydrous methanol (70 mL) at 10-20° C. This solution was added to the compound 134 solution at 5° C. The reaction mixture was heated at 40° C. for 3-4 hrs. After the completion of the reaction, the reaction mixture was concentrated under vacuum and then co-evaporated with 100 mL of anhydrous dichloromethane. The product was then dried in a vacuum oven at 40-45° C. Compound 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customThe product was then dried in a vacuum oven at 40-45° C
  4. customCompound 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC)

Quellen und Nachweise

ORD-Eintrag
ord-80d0c96ed0bc4b5ebf3b47622f4a9c60
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003659B2

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