Tetrahydrofuran → HCID 69308215, Verbindung

HRID 2250595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250595
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:12]=[C:13]([CH3:24])[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18]C(OCC)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Li+].[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:28]([C:25]1[N:11]2[N:12]=[C:13]([CH3:24])[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:34][CH2:33][OH:32])=[C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]#[N:2])[C:10]2=[CH:27][CH:26]=1)[CH3:29].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:12]=[C:13]([CH3:24])[C:14]=2[CH2:15][CH2:16][CH2:36][CH2:35][CH2:34][CH2:33][OH:32])[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydride2×HCID 9977651Ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate

Produkt 2

HCID 69307009HCID 69307009, VerbindungAusbeute 31,9 %HCID 69308215HCID 69308215, VerbindungAusbeute 64,5 %

Versuchsvorschrift

To a solution of ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (45 mg) in tetrahydrofuran (1 mL) was added lithium borohydride (5 mg) in an ice-water bath. Then the reaction mixture was stirred at ambient temperature. After 2 hours, another lithium borohydride (5 mg) was added therein and was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and was evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=1-1) to give 3-[7-ethyl-3-(6-hydroxyhexyl)-2-methylpyrrolo[1,2-b]pyridazin-4-yl]benzonitrile (26 mg, 64.5%) as an yellow oil and 6-{4-[3-(aminomethyl)phenyl]-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl}-1-hexanol (13 mg, 31.9%) as a yellow solid.

Aufarbeitung

  1. stirringwas stirred overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customwas evaporated in vacuo
  6. customThe residue was purified by p-TLC (hexane-ethyl acetate=1-1)

Quellen und Nachweise

ORD-Eintrag
ord-3925e0353166445eb0e15152156f2354
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317009B2

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