Hydrochloric Acid → [6-(3-Quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)-pyridin-2-yl]-methanol

HRID 8274

Reaktionsgleichung

Reaktionsgleichung von HRID 8274
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:12]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[C:13]3[CH2:18][CH2:17][CH2:16][N:14]3[N:15]=2)[N:6]=1)=O.[BH4-].[Li+].Cl>CO>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([C:12]2[C:11]([C:7]3[N:6]=[C:5]([CH2:3][OH:2])[CH:10]=[CH:9][CH:8]=3)=[N:15][N:14]3[CH2:16][CH2:17][CH2:18][C:13]=23)=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2×HCID 66678270Methyl 6-(3-(quinolin-4-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)picolinate

Produkt 1

HCID 10154449[6-(3-Quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)-pyridin-2-yl]-methanolAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-(3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)pyridine-2-carboxylic acid methyl ester (0.550 g, 1.48 mmol) in methanol (20 mL) is added lithium borohydride (35.5 mg, 1.63 mmol). The mixture is stirred 1 h, additional lithium borohydride (35.5 mg, 1.63 mmol) added, and the resulting mixture stirred at room temperature for 16 h. 4 N Hydrochloric acid (3 mL) is added slowly and the resulting mixture concentrated in vacuo. The residue is taken up in methanol (10 mL) and partitioned between ethyl acetate (150 mL) and saturated potassium carbonate (150 mL). The organic portion is washed with brine (150 mL), dried (magnesium sulfate), and a concentrated in vacuo. The residue is precipitated from ethyl acetate with hexanes to yield 296 mg (58%) of the title compound.

Aufarbeitung

  1. stirringthe resulting mixture stirred at room temperature for 16 h
  2. concentrationthe resulting mixture concentrated in vacuo
  3. custompartitioned between ethyl acetate (150 mL) and saturated potassium carbonate (150 mL)
  4. washThe organic portion is washed with brine (150 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationa concentrated in vacuo
  7. customThe residue is precipitated from ethyl acetate with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-01768c0751dd480d88612be8046d10c7
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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