Hydrochloric Acid → (S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril

HRID 1828350

Reaktionsgleichung

Reaktionsgleichung von HRID 1828350
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@H:14]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:24])=[O:12])=[CH:5]2.C[O-].[Na+].Br[CH2:29][C:30]#[N:31].Cl>O1CCCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@H:14]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:29][C:30]#[N:31])[C:15]1=[O:24])=[O:12])=[CH:5]2

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11534BromoacetonitrileHCID 10942334Sodium MethoxideHCID 44357926(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

Produkt 1

HCID 87730389(S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyrilAusbeute 26,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 4, 13.4 mg) was dissolved in tetrahydrofuran (5 mL) at room temperature under argon with stirring. After cooing to 0° C., sodium methoxide (4.3 mg) was added, followed 2 h later by bromoacetonitrile (7.2 mg). This was warmed to room temperature over 2 h, and 2 h later water (15 mL), 1.0 M aqueous hydrochloric acid (1 mL), and ethyl acetate (20 mL) were added. The organic phase was separated, washed with brine, and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide the title compound (4 mg). HPLC/MS [M+H]+, 379; HPLC/MS [M+Na]+, 401.

Aufarbeitung

  1. customAfter cooing to 0° C.
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter solvent evaporation under vacuum
  6. customthe crude product was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b3ef261f456e4b509481a2dfba22d5f9
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07057046B2

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