Potassium Carbonate → Methyl 3-(3-(3-(6-((2,2-difluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

HRID 1045484

Reaktionsgleichung

Reaktionsgleichung von HRID 1045484
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][N:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]3)[O:10][N:9]=2)=[CH:4][C:3]=1[NH:21][C:22]([C:24]1[N:28]2[CH:29]=[C:30]([CH2:33][O:34]S(C)(=O)=O)[CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1)=[O:23].C([O-])([O-])=O.[K+].[K+].[F:45][CH:46]([F:49])[CH2:47]O>>[F:45][CH:46]([F:49])[CH2:47][O:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]2[N:28]([C:24]([C:22]([NH:21][C:3]3[CH:4]=[C:5]([C:8]4[N:12]=[C:11]([CH:13]5[CH2:16][N:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14]5)[O:10][N:9]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])=[O:23])=[CH:25][N:26]=2)[CH:29]=1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 1361872,2-Difluoroethan-1-olHCID 86677458Methyl 3-(3-(4-methyl-3-(6-(((methylsulfonyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxamido)phenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

Produkt 1

HCID 86677462Methyl 3-(3-(3-(6-((2,2-difluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

Versuchsvorschrift

Methyl 3-(3-(4-methyl-3-(6-(((methylsulfonyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxamido)phenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (133) (15.0 mg, 0.028 mmol) and K2CO3 (8.3 mg, 0.06 mmol) in 2,2-difluoroethanol (0.5 mL) was heated at 120° C. for 5 minutes. The reaction mixture was purified by preparative HPLC to afford methyl 3-(3-(3-(6-((2,2-difluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (F95). MS m/z 527.1 (M+1)+.

Aufarbeitung

  1. customThe reaction mixture was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5395af0e6a91469fb2655b67c81bc2fc
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569283B2

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