Trifluoroacetic acid → 6-AMINO-N-(4-{4-[4-(3-CHLORO-PHENYLAMINO)-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]-PYRIMIDIN-2-YL]-PIPERAZIN-1-YL}-PHENYL)-NICOTINAMIDE TRIFLUOROACETATE

HRID 70114

Reaktionsgleichung

Reaktionsgleichung von HRID 70114
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:22]=[C:23]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=4)[C:24]4[S:29](=[O:30])[CH2:28][CH2:27][C:25]=4[N:26]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:63][C:64]1[CH:72]=[CH:71][C:67]([C:68](O)=[O:69])=[CH:66][N:65]=1.FC(F)(F)C(O)=O>CS(C)=O.C(N(C(C)C)CC)(C)C.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:63][C:64]1[CH:72]=[CH:71][C:67]([C:68]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[N:22]=[C:23]([NH:31][C:32]5[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=5)[C:24]5[S:29](=[O:30])[CH2:28][CH2:27][C:25]=5[N:26]=4)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[O:69])=[CH:66][N:65]=1

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acidHCID 184966-Aminonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66736249{2-[4-(4-amino-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-(3-chloro-phenyl)-amine trifluoroacetate

Produkt 1

HCID 667362886-AMINO-N-(4-{4-[4-(3-CHLORO-PHENYLAMINO)-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]-PYRIMIDIN-2-YL]-PIPERAZIN-1-YL}-PHENYL)-NICOTINAMIDE TRIFLUOROACETATEAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel2×

Versuchsvorschrift

200 mg of {2-[4-(4-amino-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl}-(3-chloro-phenyl)-amine trifluoroacetate are placed in 2.50 ml dimethylsulphoxide and combined with 100 μl diisopropylethylamine and 150 mg O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium-hexafluorophosphate (HATU). The mixture is stirred for 0.25 hours at ambient temperature, then 50 mg 6-aminonicotinic acid in 100 μl diisopropylethylamine are added. The reaction mixture is stirred for 16 hours at ambient temperature, then acidified with trifluoroacetic acid and 2 ml of water are added. The resulting salt is purified by preparative HPLC (method A). 140 mg of the product are obtained as the trifluoroacetate. Analytical HPLC (method B): RT=2.74 min.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 16 hours at ambient temperature
  2. additionare added
  3. customThe resulting salt is purified by preparative HPLC (method A)

Quellen und Nachweise

ORD-Eintrag
ord-d023555e36c64a98aa056f67b8f1fa8c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822474B2

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