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Hydrochloric Acid → 5-Chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

HRID 1376147
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1376147
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][CH:15]1[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:25][CH:26]3[CH2:31][O:30]C(C)(C)[O:28][CH2:27]3)[C:16]1=[O:34])=[O:13])=[CH:6]2>C1COCC1>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][CH:15]1[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:25][CH:26]([CH2:27][OH:28])[CH2:31][OH:30])[C:16]1=[O:34])=[O:13])=[CH:6]2
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 102386835-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

Produkt 1

HCID 103101385-Chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6M aqueous HCl (2.34 mL) was added to 5-chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (Example 37; 540 mg, 1.16 mmol) in THF (19 mL) and the reaction was stirred for 1 h. The reaction was quenched by addition of triethylamine (1.5 mL) and the reaction was diluted with water (20 mL) and EtOAc (40 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was triturated with hot Et2O (15 mL) and after cooling was filtered and dried to afford the title compound (421 mg, 85%) as white solid.

Aufarbeitung

  1. customThe reaction was quenched by addition of triethylamine (1.5 mL)
  2. additionthe reaction was diluted with water (20 mL) and EtOAc (40 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with hot Et2O (15 mL)
  8. temperatureafter cooling
  9. filtrationwas filtered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-04f9d429acdd44628b0d0391643c3ac0
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07169927B2

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