Morpholine → N-(2-methyl-5-(5-(morpholinomethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1045464

Reaktionsgleichung

Reaktionsgleichung von HRID 1045464
CS(O[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([NH:19][C:20]([C:22]3[N:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]4=[N:24][CH:23]=3)=[O:21])[CH:13]=2)[N:8]=1)(=O)=O.CCN(C(C)C)C(C)C.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C=O)C>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[C:7]([CH2:6][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[O:11][N:10]=2)=[CH:13][C:14]=1[NH:19][C:20]([C:22]1[N:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]2=[N:24][CH:23]=1)=[O:21]

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86677447(3-(3-(Imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl methanesulfonate

Produkt 1

HCID 71281207N-(2-methyl-5-(5-(morpholinomethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl methanesulfonate (44) (21.4 mg, 0.05 mmol), DIEA (13.0 mg, 0.1 mmol) and morpholine (13.0 mg, 0.15 mmol) in DMF (1 mL) was heated at 80° C. for 4 hours. The crude product was purified by preparative HPLC to yield N-(2-methyl-5-(5-(morpholinomethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F22). 1H NMR (400 MHz, CD2Cl2) δ 9.60 (d, J=6.8 Hz, 1H), 8.60 (d, J=1.6 Hz, 1H), 8.45 (s, 1H), 8.06 (s, 1H), 7.89 (dd, J=2.0, 8.0 Hz, 1H), 7.80 (d, J=8.8 Hz, 1H), 7.54 (m, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.15 (m, 1H), 3.93 (s, 2H), 3.75 (m, 4H), 2.67 (m, 4H), 2.48 (s, 3H). MS m/z 419.2 (M+1)+. Note: if HCl salt of morpholine (0.15 mmol) was used, AgNO3 (0.15 mmol) was needed to avoid replacement of OMs group by Cl.

Aufarbeitung

  1. customThe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-256db61cdf624be9a66dc7da3b3feb53
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569283B2

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