Ethylene Glycol → N-(5-(5-(5,8-dioxaspiro[3,4]octan-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1497913

Reaktionsgleichung

[CH2:1]([OH:4])[CH2:2][OH:3].CC1C=CC(S(O)(=O)=O)=CC=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:27]=[C:26]([CH:28]3[CH2:31][C:30](=O)[CH2:29]3)[O:25][N:24]=2)=[CH:19][C:18]=1[NH:33][C:34]([C:36]1[N:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]2=[N:38][CH:37]=1)=[O:35]>C1(C)C=CC=CC=1>[CH2:29]1[C:30]2([O:4][CH2:1][CH2:2][O:3]2)[CH2:31][CH:28]1[C:26]1[O:25][N:24]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:16])=[C:18]([NH:33][C:34]([C:36]3[N:40]4[CH:41]=[CH:42][CH:43]=[CH:44][C:39]4=[N:38][CH:37]=3)=[O:35])[CH:19]=2)[N:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Ethylene glycol (10 mg), TsOH (5 mg) and N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (10) (50 mg) were combined in toluene (3 mL) and heated at 100° C. for 5 hours. The reaction was filtered and purified by preparative reverse phase HPLC to afford N-(5-(5-(5,8-dioxaspiro[3.4]octan-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F8). 1H NMR (400 MHz, d4-MeOH) δ 9.53 (d, J=7.2 Hz, 1H), 8.50 (s, 1H), 8.13-8.12 (m, 1H), 7.90 (dd, J=8.2, 2.0 Hz, 1H), 7.75 (d, J=9.6 Hz, 1H), 7.60-7.55 (m, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.18 (ddd, J=7.2, 7.2, 1.2 Hz, 1H), 4.45-4.43 (m, 1H), 3.98-3.81 (m, 4H), 3.32-3.31 (m, 4H), 2.43 (s, 3H). MS m/z 432.1 (M+1)+.

Aufarbeitung

filtrationThe reaction was filtered
custompurified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-162a4e0939b84b5ba52af4b0fbd510d6
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09199981B2

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