Ammonia → (5S)-7-methyl-2-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one

HRID 624304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624304
[NH2:1][C@@:2]1([CH2:9][C:10]#[C:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH2:6][CH2:5][N:4]([CH3:7])[C:3]1=[O:8].N>CC#N.CO.CCOC(C)=O.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:7][N:4]1[CH2:5][CH2:6][C@:2]2([N:1]=[C:11]([C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=4)[CH:15]=[CH:14][N:13]=3)[CH2:10][CH2:9]2)[C:3]1=[O:8]

Komponenten

7

Edukt 2

HCID 222AmmoniaHCID 89648960(3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one

Produkt 1

HCID 89648866(5S)-7-methyl-2-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-oneAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 76223Silver(I) trifluoromethanesulfonateKatalysator2×HCID 887MethanolLösungsmittel2×HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Silver trifluoromethanesulphonate (564.86 mg, 2.2 mmol) was added to a solution of (3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one (which may be prepared as described in Description 11) (4.28 g, 10.99 mmol) in MeCN (60 mL) at 40° C. and the reaction was stirred for 18 hours. Additional AgOTf (10 mol %) was added and stirring was continued for 24 hrs. The solvent was evaporated and the residue was suspended in EtOAc. The organic phase was washed with water, dried (Na2SO4) and the solvent evaporated to afford a light brown oil. This was purified using an Isolera, with a (50+100) g SNAP cartridge, eluting with 0 to 100% (mixture of 1% of 2M NH3 in MeOH; 9% MeOH; 90% EtOAc) in EtOAc affording the (5S)-7-methyl-2-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (D12) (3.17 g, 8.1414 mmol, 74.1% yield) as a light brown solid;

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 24 hrs
  3. customThe solvent was evaporated
  4. washThe organic phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customto afford a light brown oil
  8. customThis was purified

Quellen und Nachweise

ORD-Eintrag
ord-df62909885024b32b59ab8c190b439a9
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303032B2

Notizen zur Reaktion

Wird geladen…