Tetrahydrofuran → HCID 69308215, compound

HRID 2250595Notes

Reaction equation

HRID 2250595 reaction equation
[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

Participants

5

Reactant 3

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

Product 2

HCID 69307009HCID 69307009, compoundYield 31.9%HCID 69308215HCID 69308215, compoundYield 64.5%

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3925e0353166445eb0e15152156f2354
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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