Hydrochloric Acid → HCID 11961741, compound

HRID 860441Notes

Reaction equation

HRID 860441 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([C:7]([CH:9]([C:20](=O)[CH3:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:25]([C:27]1[N:28]([NH2:32])[CH:29]=[CH:30][CH:31]=1)[CH3:26].C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:3]1[CH:24]=[CH:23][C:6]([C:7]2[C:29]3[N:28]([C:27]([CH2:25][CH3:26])=[CH:31][CH:30]=3)[N:32]=[C:20]([CH3:21])[C:9]=2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 143810822-ethyl-1H-pyrrol-1-amineHCID 57444530HCID 57444530, compound

Product 1

HCID 11961741HCID 11961741, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of ethyl 7-(4-cyanobenzoyl)-8-oxononanoate (2.2 g), 2-ethyl-1H-pyrrol-1-amine (809 mg), and p-toluenesulfonic acid monohydrate (64 mg) in toluene (40 ml) was refluxed for 20 minutes. The mixture was partioned between ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give the product, which was triturated with hexane to give ethyl 6-[4-(4-cyanophenyl)-7-ethyl-2-methylpyrrolo-[1,2-b]pyridazin-3-yl]hexanoate (2.21 g) as an yellow crystals.

Workup

  1. temperaturewas refluxed for 20 minutes
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)
  7. customto give the product, which
  8. customwas triturated with hexane

Sources & evidence

ORD record
ord-a23e9820886947c693580d9fad64c75f
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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