Trifluoroacetic acid → HCID 86762769, Verbindung

HRID 77582

Reaktionsgleichung

Reaktionsgleichung von HRID 77582
[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][NH:17][CH2:16][C@:14]2([C:19]2[CH:20]=[C:21]([NH:25][C:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=3)=[O:27])[CH:22]=[CH:23][CH:24]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[F:42][C:43]1[CH:44]=[N:45][C:46](Cl)=[N:47][CH:48]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17]([C:46]3[N:47]=[CH:48][C:43]([F:42])=[CH:44][N:45]=3)[CH2:16][C@:14]2([C:19]2[CH:20]=[C:21]([NH:25][C:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=3)=[O:27])[CH:22]=[CH:23][CH:24]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 81531Diisopropylethylamine3×HCID 5834662-Chloro-5-fluoropyrimidine3×HCID 86762770HCID 86762770, Verbindung

Produkt 1

HCID 86762769HCID 86762769, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of N-[3-[(4aR,7aS)-2-benzamido-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-7a-yl]phenyl]-5-fluoro-pyridine-2-carboxamide; 2,2,2-trifluoroacetic acid (150 mg, 254 μmol), 5-fluoro-2-chloropyrimidine (68 mg, 51 μmol) and diisopropylethylamine (98 μL, 56 μmol) is heated in dimethyl sulfoxide (5 mL) overnight at 40° C. Additional 5-fluoro-2-chloropyrimidine (68 mg, 51 μmol) and diisopropylethylamine (98 μL, 56 μmol) is added and the mixture is heated overnight at 50° C. Additional 5-fluoro-2-chloropyrimidine (68 mg, 51 μmol) and diisopropylethylamine (98 μL, 56 μmol) is added and the mixture is heated overnight at 50° C. for a third night. The reaction is cooled, diluted with saturated aqueous sodium carbonate (50 mL) to give a slurry that is filtered and dried in a vacuum oven at 50° C. for 4 hours to give the title compound (60 mg, 41%). ES/MS (m/e): 449 (M+H).

Aufarbeitung

  1. temperaturethe mixture is heated overnight at 50° C. for a third night
  2. temperatureThe reaction is cooled
  3. customto give a slurry that
  4. filtrationis filtered
  5. customdried in a vacuum oven at 50° C. for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-a8ead401e87b41a0ab024ab02b50ac0d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841293B1

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