Methanol → HCID 23650960, Verbindung

HRID 57122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57122
[F:1][C:2]1[CH:27]=[CH:26][C:5]2[NH:6][C:7]([C:9]3[CH:10]=[N:11][C:12]([NH:15][CH2:16][CH2:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[N:13][CH:14]=3)=[N:8][C:4]=2[C:3]=1[CH3:28].CO.[CH3:31]C1C(C=O)=CN=C(NCCCC2CCN(C)CC2)N=1.FC1C(C)=C(N)C(N)=CC=1>C1(C)C=CC=CC=1.O=[Mn]=O>[F:1][C:2]1[CH:27]=[CH:26][C:5]2[NH:6][C:7]([C:9]3[C:14]([CH3:31])=[N:13][C:12]([NH:15][CH2:16][CH2:17][CH2:18][CH:19]4[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]4)=[N:11][CH:10]=3)=[N:8][C:4]=2[C:3]=1[CH3:28]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 220555474-Fluoro-3-methylbenzene-1,2-diamineHCID 24804053[5-(5-Fluoro-4-methyl-1H-benzoimidazol-2-yl)-pyrimidin-2-yl]-[3-(1-methyl-piperidin-4-yl)-propyl]-amineHCID 462215604-Methyl-2-((3-(1-methylpiperidin-4-yl)propyl)amino)pyrimidine-5-carbaldehyde

Produkt 1

HCID 23650960HCID 23650960, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

[5-(5-Fluoro-4-methyl-1H-benzoimidazol-2-yl)-pyrimidin-2-yl]-[3-(1-methyl-piperidin-4-yl)-propyl]-amine. To a mixture of 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidin-5-yl}-methanol (0.14 g, 0.49 mmol) in toluene (3 mL) was added MnO2 (0.22 g, 2.48 mmol). After 30 min at 70° C., the mixture was filtered through diatomaceous earth. The filtrate was concentrated and immediately dissolved in DMF. A portion of this solution (corresponding to 0.05 g, 0.17 mmol of 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbaldehyde) was then treated with 4-fluoro-3-methyl-benzene-1,2-diamine (1.1 equiv.) and Na2H2S2O5 (1.25 equiv.) at 90° C. for 12 h. The reaction mixture was purified by FCC to afford the title compound. MS: mass calcd. for C22H29FN6, 396.24; m/z found, 397.2 [M+H]+. 1H NMR (CD3OD): 8.62 (s, 1H), 7.55 (dd, J=8.0, 3.9 Hz, 1H), 7.17 (dd, J=10.3, 8.8 Hz, 1H), 3.60 (t, J=6.9 Hz, 2H), 3.10-2.99 (m, 2H), 2.71 (s, 3H), 2.66 (d, J=1.4 Hz, 3H), 2.44 (s, 3H), 2.26-2.17 (m, 2H), 1.98-1.88 (m, 2H), 1.87-1.77 (m, 2H), 1.55-1.36 (m, 5H).

Aufarbeitung

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated
  3. dissolutionimmediately dissolved in DMF
  4. customThe reaction mixture was purified by FCC

Quellen und Nachweise

ORD-Eintrag
ord-ef5991f616f8450795953d3bda06effa
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434715B2

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