Propionic Acid → N-(3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)propionamide

HRID 929874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929874
[C:1]([OH:5])(=O)[CH2:2][CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:30][C:31]1[CH:32]=[C:33]([NH:37][C:38]2[CH:43]=[C:42]([NH:44][C:45]3[CH:50]=[CH:49][C:48]([O:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[CH:47][CH:46]=3)[N:41]=[CH:40][N:39]=2)[CH:34]=[CH:35][CH:36]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[O:51]([C:48]1[CH:47]=[CH:46][C:45]([NH:44][C:42]2[N:41]=[CH:40][N:39]=[C:38]([NH:37][C:33]3[CH:32]=[C:31]([NH:30][C:1](=[O:5])[CH2:2][CH3:3])[CH:36]=[CH:35][CH:34]=3)[CH:43]=2)=[CH:50][CH:49]=1)[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Komponenten

6

Edukt 4

HCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 577082883-[6-(4-Phenoxyphenylamino)-pyrimidin-4-ylamino]phenylamine

Produkt 1

HCID 57708254N-(3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of propionic acid (12 mg, 0.1 mmol) in DMF (0.6 mL) was added HATU (92 mg, 0.2 mmol) and the reaction mixture was stirred at room temperature for 30 min. To it was added N4-(3-aminophenyl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamine (60 mg, 0.1 mmol) followed by DIPEA (41 mg, 0.3 mmol) and the reaction mixture was stirred at this temperature for 16 h. It was concentrated under reduced pressure. The residue was diluted with CH2Cl2 (5 mL) and was washed with NaHCO3 solution (2 mL), water (2 mL), and brine (2 mL). Drying over Na2SO4 followed by concentration under reduced pressure offered a residue that was purified by column chromatography (SiO2, 230-400, chloroform/methanol: 9/1) to give N-(3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)propionamide (IR-10) as a brown solid. 1H NMR (DMSO-d6) δ ppm: 1.06 (t, J=7.56 Hz, 3H), 2.30 (q, J=7.48 Hz, 2H), 6.13 (s, 1H), 6.94-6.99 (m, 4H), 7.08 (t, J=7.36 Hz, 1H), 7.16-7.24 (m, 3H), 7.36 (t, J=7.44 Hz, 2H), 7.54 (d, J=8.88 Hz, 2H), 7.81 (s, 1H), 8.23 (s, 1H), 9.12 (s, 2H), 9.81 (s, 1H); LCMS: m/e 426.3 (M+1).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at this temperature for 16 h
  2. concentrationIt was concentrated under reduced pressure
  3. additionThe residue was diluted with CH2Cl2 (5 mL)
  4. washwas washed with NaHCO3 solution (2 mL), water (2 mL), and brine (2 mL)
  5. dry with materialDrying over Na2SO4
  6. concentrationfollowed by concentration under reduced pressure
  7. customwas purified by column chromatography (SiO2, 230-400, chloroform/methanol: 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-13dca26ff7114ab1b1c2843d194d1dee
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296704B2

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