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

반응식

HRID 70114 반응식
[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

참가 물질

8

반응물 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

생성물 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 TRIFLUOROACETATE수율 57.8%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 81531Diisopropylethylamine용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d023555e36c64a98aa056f67b8f1fa8c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822474B2

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