Diisopropylethylamine → HCID 178461977, Verbindung

HRID 75336

Reaktionsgleichung

Reaktionsgleichung von HRID 75336
[CH:1]1([N:4]2[C:8]([C:9]3[CH:10]=[C:11]4[N:20]([CH3:21])[CH:19]=[CH:18][C:12]4=[N:13][C:14]=3[C@@H:15]([NH2:17])[CH3:16])=[CH:7][CH:6]=[N:5]2)[CH2:3][CH2:2]1.Cl[C:23]1[N:31]=[C:30]([NH2:32])[N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][NH:27]2.C(N(C(C)C)C(C)C)C>C(#N)C>[CH:1]1([N:4]2[C:8]([C:9]3[CH:10]=[C:11]4[N:20]([CH3:21])[CH:19]=[CH:18][C:12]4=[N:13][C:14]=3[C@@H:15]([NH:17][C:23]3[N:31]=[C:30]([NH2:32])[N:29]=[C:28]4[C:24]=3[N:25]=[CH:26][NH:27]4)[CH3:16])=[CH:7][CH:6]=[N:5]2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 86707997(S)-1-(6-(1-Cyclopropyl-1H-pyrazol-5-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamineHCID 1785084356-chloro-1H-purin-2-amine

Produkt 1

HCID 178461977HCID 178461977, VerbindungAusbeute 9,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

(S)-1-(6-(1-Cyclopropyl-1H-pyrazol-5-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (166 mg, 0.590 mmol), 6-chloro-9H-purin-2-amine (100 mg, 0.590 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.31 mL, 1.8 mmol) were combined in acetonitrile (6 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 2 hours and then concentrated. The residue was taken up in DMF and was purified by preparative HPLC (acid mode) eluting with 10-15% ACN in water. The fractions containing the desired compound were combined and concentrated in vacuo. The residue was further purified by preparative HPLC (basic mode) eluting with 25-35% ACN in water. The fractions containing the desired product were combined and concentrated in vacuo to give the title compound as a white solid (23 mg, 9.2%). 1H NMR (500 MHz, CD3OD) δ ppm 0.59-0.75 (m, 2 H), 0.87-1.03 (m, 2H), 1.50 (d, J=6.35 Hz, 3 H), 3.38-3.47 (m, 1 H), 3.87 (d, J=0.98 Hz, 3 H), 5.56 (br s, 1 H), 6.44 (s, 1 H), 6.70 (d, J=2.93 Hz, 1 H), 7.54-7.71 (m, 3 H), 7.83 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for C21H22N10, 415; found 415.

Aufarbeitung

  1. concentrationconcentrated
  2. customwas purified by preparative HPLC (acid mode)
  3. washeluting with 10-15% ACN in water
  4. additionThe fractions containing the desired compound
  5. concentrationconcentrated in vacuo
  6. customThe residue was further purified by preparative HPLC (basic mode)
  7. washeluting with 25-35% ACN in water
  8. additionThe fractions containing the desired product
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2083d501cb344b00acd834e792c71cac
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835420B2

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