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methyl 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate → 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylic acid

HRID 1399795
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1399795
[CH3:1][C:2]1[N:20]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[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[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[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]([OH:12])=[O:11])=[C:4]2[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 89648052methyl 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate

Produkt 1

HCID 716105572-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylic acidAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3939Lithium HydroxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of methyl 2-methyl-5-morpholino-3-(naphthalen-1-ylmethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate (134 mg, 0.32 mmol) in 2N LiOH (15 mL) and THF (15 mL) was stirred at 50° C. for 5 h. It was cooled to room temperature and the precipitate was collected by filtration. It was then poured into water (100 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 crude product. It was then made a further purification by prep-HPLC to afford the desired product as a yellow solid (64 mg, 50%); LC/MS: MS (ES+) m/e 403 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.63 (s, 3H), 3.48 (t, J=4.2 Hz, 4H), 3.65 (t, J=4.2 Hz, 4H), 6.03 (s, 2H), 6.97 (d, J=7.8 Hz, 1H), 7.28 (s, 1H), 7.42 (t, J=7.5 Hz, 1H), 7.58-7.67 (m, 2H), 7.91 (d, J=7.8 Hz, 1H), 8.01 (d, J=7.8 Hz, 1H), 8.33 (d, J=7.8 Hz, 1H).

Aufarbeitung

  1. temperatureIt was cooled to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionIt was then poured into water (100 mL)
  4. filtrationIt was filtered
  5. customthe solid was purified by chromatography on silica gel
  6. washeluted with MeOH/DCM=1/5
  7. customto afford the crude product
  8. customa further purification by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-de7a83c4f1b8414a8f289a2c8eef8f8b
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906910B2

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