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Sodium Hydroxide → Ethyl 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-4-piperidinecarboxylate

HRID 1512787
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512787
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:13][C:14]1[CH:15]=[C:16]([C:24]2[O:28][N:27]=[C:26]([C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:37]=3[N:36]([CH3:38])[CH:35]=[C:34]4[CH:39]=O)[N:25]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([CH3:23])[CH3:22].[OH-].[Na+]>C(O)C>[Cl:13][C:14]1[CH:15]=[C:16]([C:24]2[O:28][N:27]=[C:26]([C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:37]=3[N:36]([CH3:38])[CH:35]=[C:34]4[CH2:39][N:2]3[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]3)[N:25]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([CH3:22])[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 18521570Ethyl 4-piperidinecarboxylate hydrochlorideHCID 591461277-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde

Produkt 1

HCID 59146087Ethyl 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-4-piperidinecarboxylateAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 4-piperidinecarboxylate hydrochloride (969 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (396 mg) was added to a solution of NaOH (200 mg) in ethanol (10 mL). After stirring for 0.5 hour, ethanol was evaporated off and then dichloromethane (40 mL) containing AcOH (0.5 mL) was added to the residue. NaBH(OAc)3 (1.06 g) was added to the above mixture. The reaction mixture was stirred at room temperature overnight and then terminated by saturated NaHCO3 solution. The organic layer was separated and washed with water and brine. After the solvent was evaporated off the residue was purified by Mass Directed AutoPrep to afford ethyl 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-4-piperidinecarboxylate (D79) (308 mg) as a yellow solid. MS (ES): C29H33ClN4O4 requires 536; found 537.3 (M+H+).

Aufarbeitung

  1. customethanol was evaporated off
  2. additiondichloromethane (40 mL) containing AcOH (0.5 mL)
  3. additionwas added to the residue
  4. additionNaBH(OAc)3 (1.06 g) was added to the above mixture
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. customterminated by saturated NaHCO3 solution
  7. customThe organic layer was separated
  8. washwashed with water and brine
  9. customAfter the solvent was evaporated off the residue
  10. customwas purified by Mass Directed AutoPrep

Quellen und Nachweise

ORD-Eintrag
ord-51da6a158cb440c096dc80d13d96763f
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217028B2

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