Dimethylformamide → (S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl trifluoromethanesulfonate

HRID 1970333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970333
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([OH:26])=[CH:10][CH:11]=3)[N:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.C1C=CC(N[S:45]([C:48]([F:51])([F:50])[F:49])(=[O:47])=[O:46])=CC=1>O>[F:49][C:48]([F:51])([F:50])[S:45]([O:26][C:9]1[CH:8]=[C:7]2[C@@:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:6]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH:18]=3)[O:13][C:12]2=[CH:11][CH:10]=1)(=[O:47])=[O:46]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 67248031(S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-7-ol

Produkt 1

HCID 86640725(S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl trifluoromethanesulfonateAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A vial charged with (S)-2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-7-ol (0.200 g, 0.572 mmol) and potassium carbonate (0.087 g, 0.630 mmol) was treated with 2 mL DMF and was allowed to stir for 15 minutes. The reaction mixture was cooled to 0° C. and n-phenyltriflamide (0.245 g, 0.630 mmol) was added. After stirring for one hour the reaction mixture was poured into water and extracted with EtOAc. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography gave (S)-2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (0.183 g, 0.380 mmol, 66.4% yield)

Aufarbeitung

  1. stirringAfter stirring for one hour the reaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialThe organics were dried over MgSO4
  4. concentrationconcentrated
  5. customPurification of the crude residue by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-42b2b0635e99495d8493624dd8442e27
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426447B2

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