Sodium Bicarbonate → [3-((R)-5-Amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-(3-bromo-[1,7]naphthyridin-8-yl)-amine

HRID 925460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925460
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C@:12]([C:17]2[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:18]=2[F:24])([CH:14]([F:16])[F:15])[N:13]=1)(C)(C)C.[Br:26][C:27]1[CH:28]=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[N:32][C:31]=2Cl.C([O-])(O)=O.[Na+]>C(O)(C)(C)C.Cl.O1CCOCC1>[NH2:7][C:8]1[CH2:9][O:10][CH2:11][C@:12]([C:17]2[CH:22]=[C:21]([NH:23][C:31]3[N:32]=[CH:33][CH:34]=[C:35]4[C:30]=3[N:29]=[CH:28][C:27]([Br:26])=[CH:36]4)[CH:20]=[CH:19][C:18]=2[F:24])([CH:14]([F:15])[F:16])[N:13]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 66666080[(R)-5-(5-Amino-2-fluoro-phenyl)-5-difluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl esterHCID 722135923-Bromo-8-chloro-1,7-naphthyridine

Produkt 1

HCID 71549953[3-((R)-5-Amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-(3-bromo-[1,7]naphthyridin-8-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

[(R)-5-(5-Amino-2-fluoro-phenyl)-5-difluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]carbamic acid tert-butyl ester (CAS registry 1262859-09-5) (250 mg, 0.696 mmol) and 3-bromo-8-chloro-[1,7]naphthyridine [Heteroaryl 1] (186 mg, 0.765 mmol) were dissolved in tert-Butanol (4 ml) in a microwave vial and HCl (0.174 ml of a 4M solution in dioxane) was added. The vial was sealed and heated to 100° C. for 1 h. The reaction mixture was cooled to rt and added to a saturated NaHCO3 solution (20 ml) and stirred at rt for 10 min.

Aufarbeitung

  1. additionwas added
  2. customThe vial was sealed
  3. temperatureThe reaction mixture was cooled to rt

Quellen und Nachweise

ORD-Eintrag
ord-43829f67077540bcaf0b7c1bb4d07895
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284284B2

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