3-Aminopyridine → HCID 25014405, Verbindung

HRID 421742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421742
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.C[N:9](C1C=CC=CC=1)[S:10]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[CH:33]=[CH:32][C:21]3=[N:22][CH:23]=[C:24]([C:26]4[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=4)[CH:25]=[C:20]3[C:19](=[O:34])[C:18]=2[CH:35]=1)(=[O:12])=[O:11].N1C=CC=C(N)C=1>CS(C)=O.O>[CH3:31][N:29]1[CH:30]=[C:26]([C:24]2[CH:25]=[C:20]3[C:19](=[O:34])[C:18]4[CH:35]=[C:14]([CH2:13][S:10]([NH:9][C:3]5[CH:1]=[N:2][CH:6]=[CH:5][CH:4]=5)(=[O:12])=[O:11])[CH:15]=[CH:16][C:17]=4[CH:33]=[CH:32][C:21]3=[N:22][CH:23]=2)[CH:27]=[N:28]1

Komponenten

6

Edukt 3

HCID 100093-AminopyridineHCID 13387N-methyl-2-pyrrolidoneHCID 25014404HCID 25014404, Verbindung

Produkt 1

HCID 25014405HCID 25014405, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

N-Methyl-2-pyrrolidinone (3 ml) was added to N-methyl-1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-phenylmethanesulfonamide (150 mg, 0.319 mmol) and pyridin-3-amine (150 mg, 1.594 mmol) in a vial. The vial was sealed and the resulting solution was heated to 180° C. with stirring. After 2.25 h., the reaction was cooled to room temperature and diluted in DMSO and water. The resulting solution was filtered and purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford the title compound as a brown solid. 1H NMR (600 MHz, DMSO-D6) δ 9.21 (d, 1H); 8.52 (d, 1H); 8.48 (s, 1H); 8.33 (d, 1H); 8.16 (d, 1H); 8.15 (s, 1H); 8.07 (s, 1H); 7.77 (d, 1H); 7.68 (dd, 1H); 7.52 (m, 1H); 7.35 (d, 1H); 7.32 (d, 1H); 7.25 (m, 1H); 4.77 (s, 2H); 3.89 (s, 3H). LRMS (APCI) calculated for C24H19N5O3S [M+H]+, 458.1; found 458.1.

Aufarbeitung

  1. customThe vial was sealed
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationThe resulting solution was filtered
  4. custompurified by preparative HPLC Reverse phase (C-18)
  5. washeluting with Acetonitrile/Water+0.05% TFA

Quellen und Nachweise

ORD-Eintrag
ord-0fbce1ef6b9745cea486eb23a7c0ff29
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101603B2

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