Ethanol → HCID 178434683, Verbindung

HRID 1505000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505000
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([F:22])[F:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25]1[C:29]([CH3:30])=[C:28]([NH2:31])[NH:27][N:26]=1.CCO>Cl.CC#N>[ClH:23].[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([F:22])[F:21])[N:14]=[CH:13][CH:12]=[C:11]2[NH:31][C:28]1[NH:27][N:26]=[C:25]([CH3:24])[C:29]=1[CH3:30])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 90047095HCID 90047095, VerbindungHCID 178434631HCID 178434631, Verbindung

Produkt 1

HCID 178434683HCID 178434683, VerbindungAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 6-(tert-butylsulfonyl)-4-chloro-7-(2,2-difluoroethoxy)quinoline (85 mg, 0.234 mmol) and 3,4-dimethyl-1H-pyrazol-5-amine (33.8 mg, 0.304 mmol) in a microwave vial was added EtOH (779 μl) followed by 1 drop of 1N aq HCl (8.52 mg, 0.234 mmol). The vial was sealed and heated to 80° C. behind a blast shield overnight. LCMS showed full conversion to product. Concentrated reaction and triturated resulting residue with ˜2 mL of MeCN using ˜1 min of sonication. Filtered resulting solid, rinsing with MeCN, and dried under vacuum resulting in the product 6-(tert-butylsulfonyl)-7-(2,2-difluoroethoxy)-N-(3,4-dimethyl-1H-pyrazol-5-yl)quinolin-4-amine, hydrochloride (93.5 mg, 0.197 mmol, 84% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.70 (s, 1H), 11.25 (br. s., 1H), 9.26 (br. s., 1H), 8.51 (d, J=7.07 Hz, 1H), 7.57 (s, 1H), 6.67 (d, J=7.33 Hz, 1H), 6.47 (tt, J=3.28, 53.81 Hz, 1H), 4.63 (td, J=3.16, 14.46 Hz, 2H), 2.24 (s, 3H), 1.84 (s, 3H), 1.34 (s, 9H). MS: m/z: 439.3 [M+H]+.

Aufarbeitung

  1. customThe vial was sealed
  2. concentrationConcentrated
  3. customreaction
  4. customtriturated
  5. customresulting residue
  6. filtrationFiltered
  7. customresulting solid
  8. washrinsing with MeCN
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1ccf77b2082141058e80bc5b264c1f7c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216965B2

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