2-ethyl-1H-pyrrol-1-amine → Ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate

HRID 860431Notes

Reaction equation

HRID 860431 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[C:6]([CH:8]([C:18](=O)[CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)#[N:2].[CH2:24]([C:26]1[N:27]([NH2:31])[CH:28]=[CH:29][CH:30]=1)[CH3:25]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[C:28]3[N:27]([C:26]([CH2:24][CH3:25])=[CH:30][CH:29]=3)[N:31]=[C:18]([CH3:19])[C:8]=2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:21]=[CH:22][CH:23]=1)#[N:2]

Participants

5

Reactant 2

HCID 143810822-ethyl-1H-pyrrol-1-amineHCID 57444485HCID 57444485, compound

Product 1

HCID 9977651Ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoateYield 83.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of ethyl 6-(3-cyanobenzoyl)-7-oxooctanoate (3.18 g) in toluene (30 mL) was added 2-ethyl-1H-pyrrol-1-amine (1.17 g) and p-toluenesulfonic acid monohydrate (96 mg) at ambient temperature. The reaction mixture was refluxed for 1 hour. The mixture was evaporated in vacuo. The residue was purified by flash silica gel chromatography (silica gel, 200 mL) eluting with hexane-ethyl acetate=20-1, 15-1, and 10-1 to give ethyl 5-[4-(3-cyanophenyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (3.29 g, 83.8%) as an yellow oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customThe mixture was evaporated in vacuo
  3. customThe residue was purified by flash silica gel chromatography (silica gel, 200 mL)
  4. washeluting with hexane-ethyl acetate=20-1, 15-1, and 10-1

Sources & evidence

ORD record
ord-724f678fc08d46cb991e0ebfb59506ed
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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