Ammonium Chloride → HCID 68772647, Verbindung

HRID 1628419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628419
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:13]=[N:14][C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:16][C:17]=3[CH3:18])[N:7]([CH2:24][CH2:25][CH2:26][C:27](OCC)=[O:28])[C:6]=2[C:5]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:4][CH:3]=1.[BH4-].[Li+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[CH:13]=[N:14][C:15]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:16][C:17]=3[CH3:18])[N:7]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[C:6]=2[C:5]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 68761864Ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(4-methyl-6-pyrrolidin-1-ylpyridin-3-yl)amino]-1H-benzimidazol-1-yl}butanoate

Produkt 1

HCID 68772647HCID 68772647, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-{4-chloro-7-(1-ethylpropyl)-2-[(4-methyl-6-pyrrolidin-1-ylpyridin-3-yl)amino]-1H-benzimidazol-1-yl}butanoate (650 mg, 1.27 mmol) in tetrahydrofuran (5 mL) was added lithium borohydride (84 mg, 3.82 mmol) portionwise at 0° C. The mixture was warmed to room temperature and stirred for 24 hr. Aqueous ammonium chloride was added and the mixture was stirred for 30 minutes followed by addition of aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a light brown solid, which was recrystallized from ethyl acetate/isopropyl ether to give the title compound (375 mg, 0.798 mmol, 63%) as a colorless solid.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a light brown solid, which
  7. customwas recrystallized from ethyl acetate/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-584c4dd01e964ade91afb43e16ff0123
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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