Acetic Acid → 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid

HRID 882219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882219
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][N:26]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 70976482methyl 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Produkt 1

HCID 709764624-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 3) (1.0 g, 2.270 mmol) in MeOH (15 mL) at room temperature was treated with aqueous sodium hydroxide solution (2N, 2.27 mL, 4.54 mmol) and the resulting mixture was stirred at this temperature for 24 h. The bulk of MeOH was evaporated in vacuo and the aqueous residue was treated with acetic acid (0.39 mL, 6.81 mmol) giving precipitate which was isolated by filtration and dried under vacuum at 40° C. to afford 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (820 mg, 1.923 mmol, 85% yield) as a yellow solid. LCMS (HpH, 2 min), Rt=0.64 min, MH+=427.

Aufarbeitung

  1. customat room temperature
  2. customThe bulk of MeOH was evaporated in vacuo
  3. customgiving precipitate which
  4. customwas isolated by filtration
  5. customdried under vacuum at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-c01bd8c78a6b4866863ac24155e9cfda
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993554B2

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