Sodium Bicarbonate → HCID 68152353, Verbindung

HRID 593357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593357
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[CH2:7][CH2:8][C:9]=2[CH:10]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:27])=[C:17]([C@@:19]2([CH3:26])[NH:24][C:23](=[O:25])[CH2:22][O:21][CH2:20]2)[CH:18]=1.[B][B][B][B][B][B][B][B][B][B].C(=O)([O-])O.[Na+]>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([F:27])=[C:17]([C@@:19]4([CH3:26])[NH:24][C:23](=[O:25])[CH2:22][O:21][CH2:20]4)[CH:18]=3)[CH2:7][CH2:8][C:9]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 58082858HCID 58082858, VerbindungHCID 58155273(R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-oneHCID 178419135HCID 178419135, Verbindung

Produkt 1

HCID 68152353HCID 68152353, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-5,6-dihydro-[1]pyrindin-7-one (34.5 mg, 0.21 mmol) and (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-morpholin-3-one (50.1 mg, 0.22 mmol) in a mixture of methanol (7.3 ml) and dichloromethane (0.9 ml) was treated with decaborane (6.9 mg, 0.21 mmol). The reaction mixture was stirred at room temperature for 22 hours. For the workup, the mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, thereafter extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate, then evaporated at reduced pressure. The crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 20:80 as the eluent. The (R)-5-[5-((RS)-3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one was obtained as an orange solid (50 mg, 71%); (calculated) C19H19ClFN3O2 [375.83]; (found) [M]+=376, [M+2]+=378.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated at reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 20:80 as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-3d47638cfddb4a2f8b6143417c993357
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242943B2

Notizen zur Reaktion

Wird geladen…