Hydrochloric Acid → 1-{[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylic acid

HRID 1512932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512932
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[C:26]4[C:22]([C:23]([CH2:28][N:29]5[CH2:34][CH2:33][CH:32]([C:35]([O:37]CC)=[O:36])[CH2:31][CH2:30]5)=[CH:24][NH:25]4)=[CH:21][CH:20]=3)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].Cl>CC(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:27]=[C:26]4[C:22]([C:23]([CH2:28][N:29]5[CH2:34][CH2:33][CH:32]([C:35]([OH:37])=[O:36])[CH2:31][CH2:30]5)=[CH:24][NH:25]4)=[CH:21][CH:20]=3)[N:15]=2)[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58222435Ethyl 1-{[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylate

Produkt 1

HCID 445468581-{[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium hydroxide (19 mg) was added to a solution of ethyl 1-{[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylate (D103) (134 mg) in iPrOH (4 mL) and water (4 mL). The resulting mixture was heated at 70° C. for 40 mins. Then 0.5 M HCl solution was added until pH was about 6. The solvent was concentrated, and the residue was dissolved in water. The precipitated solid was purified by Mass Directed Auto Prep to afford 1-{[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylic acid (E78) (118 mg) as a pale red-white solid. δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 1.55 (2H, m), 1.77 (2H, m), 2.01 (2H, m), 2.18 (1H, m), 2.85 (2H, m), 3.67 (2H, m), 5.46 (1H, m), 7.46 (1H, s), 7.73 (1H, dd), 7.81 (1H, d), 8.14 (1H, s), 8.56 (1H, d), 8.94 (1H, d), 11.37 (1H, s), 12.02 (1H, br s). MS (ES): C26H26ClN6O4 requires 495; found 496.2 (M+H+).

Aufarbeitung

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in water
  3. customThe precipitated solid was purified by Mass Directed Auto Prep

Quellen und Nachweise

ORD-Eintrag
ord-93a5bf21d11044878bda3a8427306410
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217028B2

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