Trifluoroacetic acid → 3-[(2-Amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}-pyrimidin-4-yl)amino]propan-1-ol

HRID 16457

Reaktionsgleichung

Reaktionsgleichung von HRID 16457
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[CH:25][C:18]=34)=[C:12]([F:26])[CH:11]=2)[CH:3]=1.C[O:28][C:29]1C=C(OC)C=C[C:30]=1[CH2:31][NH:32]CCCO.C(O)(C(F)(F)F)=O.C(OCC)(=O)C>C(O)CCC.C(N(C(C)C)C(C)C)C.C(Cl)Cl>[NH2:8][C:6]1[N:7]=[C:2]([NH:32][CH2:31][CH2:30][CH2:29][OH:28])[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[CH:25][C:18]=34)=[C:12]([F:26])[CH:11]=2)[N:5]=1

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 109661863-[(2,4-Dimethoxybenzyl)amino]propan-1-olHCID 587332416-Chloro-N4-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]pyrimidine-2,4-diamine

Produkt 1

HCID 179792883-[(2-Amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}-pyrimidin-4-yl)amino]propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2631-ButanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

78 mg (0.21 mmol) of 6-chloro-N4-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenyl]pyrimidine-2,4-diamine (from example 60), 190 mg (0.84 mmol) of 3-[(2,4-dimethoxybenzyl)amino]propan-1-ol in 1 ml of 1-butanol and 0.37 ml of N-ethyl-diisopropylamine are, in a closed pressure vessel, heated at 130° C. overnight. Volatile components are removed under reduced pressure, and the residue is purified by preparative HPLC. The substrate obtained is taken up in 2 ml of DCM, and 0.5 ml of TFA is added. The mixture is stirred at RT for 20 min and then poured into ethyl acetate and extracted with sat. sodium carbonate solution. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

Aufarbeitung

  1. customVolatile components are removed under reduced pressure
  2. customthe residue is purified by preparative HPLC
  3. customThe substrate obtained
  4. extractionextracted with sat. sodium carbonate solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d15089b0ff284eaf876b69e07ef3cd4b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737153B2

Verknüpfte Notizen

Wird geladen…