Diisopropylcarbodiimide → US10251893, Cpd 221

HRID 592255

Reaktionsgleichung

Reaktionsgleichung von HRID 592255
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][C:16]([OH:18])=O)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=2)[N:20]=1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][C:16]([NH:31][C:28]3[CH:27]=[CH:26][C:25]([C:21]4[N:20]=[N:19][CH:24]=[CH:23][CH:22]=4)=[CH:30][N:29]=3)=[O:18])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 584476635-(Pyridazin-3-yl)pyridin-2-amineHCID 584476922-(2'-Fluoro-3-methyl-2,4'-bipyridin-5-yl)acetic acid

Produkt 1

HCID 46927368US10251893, Cpd 221

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the mixture of 2-(2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)acetic acid 193-2 (25 mg, 0.1 mmol) and 5-(pyridazin-3-yl)pyridin-2-amine 145-3 (17 mg, 0.1 mmol) in DCM (1 mL) was added N,N′-Diisopropylcarbodiimide (22 μL, 0.15 mmol) at room temperature. The mixture was stirred at room temperature for 24 hours. The solvent was removed by rotary evaporation and the residue was dissolved in DMSO and then purified by reverse-phase HPLC to give 2-(2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)-N-(5-(pyrazin-2-yl)pyridin-2-yl)acetamide 221 as white solid. MS m/z 401.1 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 11.09 (s, 1H), 9.17 (dd, 1H), 9.07 (d, 1H), 8.51 (dd, 1H), 8.46 (d, 1H), 8.28 (d, 1H), 8.25 (dd, 1H), 8.18 (d, 1H), 7.76 (m, 1H), 7.71 (d, 1H), 7.51 (m, 1H), 7.31 (s, 1H), 3.83 (s, 2H), 2.31 (s, 3H).

Aufarbeitung

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was dissolved in DMSO
  3. custompurified by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-78cea9b2d79b4c758311347b5103ae16
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238646B2

Verknüpfte Notizen

Wird geladen…