methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate → 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

HRID 1399789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399789
[CH3:1][C:2]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=2[CH3:32])[C:5]2=[N:6][C:7]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:8][C:9]([C:10]([O:12]C)=[O:11])=[C:4]2[N:3]=1>[Li+].[OH-].C1COCC1>[CH3:1][C:2]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[C:23]=2[CH3:32])[C:5]2=[N:6][C:7]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[C:4]2[N:3]=1

Komponenten

4

Edukt 1

HCID 89648239methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

Produkt 1

HCID 716125532-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylic acidAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3939Lithium HydroxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of methyl 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate (310 mg, 0.69 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 50° C. for 8 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (50 mL) and the suspension was acidified with formic acid to pH=1. It was filtered and the solid was purified by chromatography on silica gel eluted with MeOH/DCM=1/5 to afford the desired product as a gray solid (184 mg, 61%); LC/MS: MS (ES+) m/e 435 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.54 (s, 3H), 2.79 (s, 3H), 3.51 (s, 4H), 3.67 (s, 4H), 5.67 (s, 2H), 7.20 (d, J=10.2 Hz, 1H), 7.35 (t, J=7.8 Hz, 1H), 7.42 (s, 1H), 7.69 (d, J=10.2 Hz, 1H).

Aufarbeitung

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (50 mL)
  4. filtrationIt was filtered
  5. customthe solid was purified by chromatography on silica gel
  6. washeluted with MeOH/DCM=1/5

Quellen und Nachweise

ORD-Eintrag
ord-d9da61bff2cf49fa9fffe0174e3fdc98
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906910B2

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