Sodium Hydroxide → 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid

HRID 1403459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1403459
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[C:20]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:27]([O:29]C)=[O:28])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[C:20]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:27]([OH:29])=[O:28])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 70665283methyl 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate

Produkt 1

HCID 706648652-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acidAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (140 mg, 0.35 mmol) in methanol (30 mL) and water (2 mL) was added sodium hydroxide (56 mg, 1.40 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (30 mL) and adjusted to pH 5 with acetic acid. The solids were collected by filtration to afford 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid as a light yellow solid (100 mg, 74%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30 mL)
  3. filtrationThe solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-bfd259ebc12547c5b3d42cf3d4e18045
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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