Triethylamine → HCID 178477691, Verbindung

HRID 1888215

Reaktionsgleichung

Reaktionsgleichung von HRID 1888215
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:15][CH2:16][N:17]([S:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[CH2:18][CH2:19]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 178513507HCID 178513507, Verbindung2×

Produkt 1

HCID 178477691HCID 178477691, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The crude 5-bromo-3-(4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 6) (1.23 mmol) was suspended in dichloromethane (20 mL) and treated with triethyl amine (0.856 mL, 6.15 mmols), and ethane sulfonyl chloride (0.175 mL, 1.85 mmols) at 0° C. After 2 hrs, the mixture was concentrated to dryness in vacuo at ambient temperature, treated with water (25 mL), and extracted with dichloromethane (100 mL). The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a light brown solid. This was purified by combiflash (column 10 g, eluting with 100% dichloromethane, 5% ethyl acetate/dichloromethane, 30% ethyl acetate/dichloromethane) to give the title compound (0.161 g, 32%).

Aufarbeitung

  1. concentrationthe mixture was concentrated to dryness in vacuo at ambient temperature
  2. additiontreated with water (25 mL)
  3. extractionextracted with dichloromethane (100 mL)
  4. washThe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light brown solid
  9. customThis was purified by combiflash (column 10 g, eluting with 100% dichloromethane, 5% ethyl acetate/dichloromethane, 30% ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0081fca7190c4de389e3dac092b153f7
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501780B2

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