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Hydrochloric Acid → 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1-methyl-1H-indol-3-yl]propanoic acid

HRID 1512882
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512882
[CH2:1]1N2CCN(CC2)C1.[Cl:9][C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[CH:27][C:28]([F:39])=[C:29]4[C:33]=3[NH:32][CH:31]=[C:30]4[CH2:34][CH2:35][C:36]([OH:38])=[O:37])[N:21]=2)[CH:13]=[N:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18].[OH-].[Na+].Cl>CN(C=O)C.C(=O)(OC)OC.C1COCC1.O>[Cl:9][C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[CH:27][C:28]([F:39])=[C:29]4[C:33]=3[N:32]([CH3:1])[CH:31]=[C:30]4[CH2:34][CH2:35][C:36]([OH:38])=[O:37])[N:21]=2)[CH:13]=[N:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 14798Sodium HydroxideHCID 445477603-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1H-indol-3-yl]propanoic acid

Produkt 1

HCID 445477613-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1-methyl-1H-indol-3-yl]propanoic acid
Ausbeute 36,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 12021Dimethyl CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
94 °C

Versuchsvorschrift

DABCO (45 mg) was added to a solution of 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1H-indol-3-yl]propanoic acid (E22) (71 mg) in DMF (2 mL) and dimethyl carbonate (2 mL). The reaction mixture was stirred at 94° C. for 3 days. Then the reaction was quenched with water, and extracted with EtOAc for 3 times. The combined organic solution was washed with brine, and dried over anhydrous sodium sulfate. The dried solution was concentrated to afford the crude product as a brown solid. This solid was dissolved in THF (3 mL) and water (3 mL). Sodium hydroxide (40 mg) was then added to the mixture. The reaction mixture was stirred at 90° C. for 1 hour. Then 0.5 M HCl 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 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-4-fluoro-1-methyl-1H-indol-3-yl]propanoic acid (E23) (27 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.38 (6H, d), 2.60 (2H, t), 3.03 (2H, t), 3.63 (3H, s), 5.45 (1H, m), 6.96 (1H, dd), 7.22 (1H, s), 7.42 (1H, dd), 8.57 (1H, d), 8.94 (1H, d), 12.11 (1H, br s). δF (DMSO-d6, 376 MHz): −120.4. MS (ES): C22H20ClFN4O4 requires 458; found 459.1 (M+H+).

Aufarbeitung

  1. customThen the reaction was quenched with water
  2. extractionextracted with EtOAc for 3 times
  3. washThe combined organic solution was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried solution was concentrated
  6. customto afford the crude product as a brown solid
  7. stirringThe reaction mixture was stirred at 90° C. for 1 hour
  8. concentrationThe solvent was concentrated
  9. dissolutionthe residue was dissolved in water
  10. customThe precipitated solid was purified by Mass Directed Auto Prep

Quellen und Nachweise

ORD-Eintrag
ord-814428d4678a4f49b01fe9501bcee724
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217028B2

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