Dicyclohexylcarbodiimide → 2-Methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide

HRID 592187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592187
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH3:19])[C:8]([C:11]2[CH:16]=[CH:15][N+:14]([O-:17])=[C:13]([CH3:18])[CH:12]=2)=[N:9][CH:10]=1)([OH:3])=O.[N:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:18][C:13]1[CH:12]=[C:11]([C:8]2[C:7]([CH3:19])=[CH:6][C:5]([CH2:4][C:1](=[O:3])[NH:32][C:29]3[CH:28]=[CH:27][C:26]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][N:20]=4)=[CH:31][N:30]=3)=[CH:10][N:9]=2)[CH:16]=[CH:15][N+:14]=1[O-:17]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 592592255-(Pyrazin-2-yl)pyridin-2-amineHCID 671347314-(5-(Carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide

Produkt 1

HCID 584479182-Methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(5-(carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide 156-6 from Step 4 (0.41 mmol), 5-(pyrazin-2-yl)pyridin-2-amine 86-3 (141 mg, 0.82 mmol), 1,3-dicyclohexylcarbodiimide (188 mg, 0.90 mmol) and 4-(dimethylamino)pyridine (16 mg, 0.16 mmol) in DMF (2 mL) was stirred at room temperature for 10 hours. The crude product was filtered to remove the insoluble and the filtrate was purified by reverse phase HPLC to give 2-methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide 156 as white solid. MS m/z 413.2 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 11.12 (s, 1H), 9.31 (d, 1H), 9.11 (d, 1H), 8.72 (m, 1H), 8.62 (d, 1H), 8.52 (dd, 1H), 8.48 (d, 1H), 8.31 (d, 1H), 8.21 (d, 1H), 7.73 (m, 2H), 7.52 (dd, 1H), 3.86 (s, 2H), 2.41 (s, 3H), 2.40 (s, 3H).

Aufarbeitung

  1. filtrationThe crude product was filtered
  2. customto remove the insoluble and the filtrate
  3. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-85b2ced6f51e4bd8b0ed8dbe853983f4
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238646B2

Notizen zur Reaktion

Wird geladen…