Triethyl methanetricarboxylate → 1-Butyl-4-hydroxy-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

HRID 1511959Notes

Reaction equation

HRID 1511959 reaction equation
[CH2:1]([NH:5][N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)[CH2:2][CH2:3][CH3:4].[CH2:11]([O:13][C:14](=[O:26])[CH:15]([C:21](OCC)=[O:22])[C:16](OCC)=[O:17])[CH3:12]>>[CH2:11]([O:13][C:14]([C:15]1[C:16](=[O:17])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:6]2[CH:10]=[CH:9][CH:8]=[C:7]2[C:21]=1[OH:22])=[O:26])[CH3:12]

Participants

3

Reactant 2

HCID 80471Triethyl methanetricarboxylateHCID 67230608HCID 67230608, compound

Product 1

HCID 672309931-Butyl-4-hydroxy-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

Conditions

Temperature
170 °C

Procedure

A mixture of butyl-pyrrol-1-yl-amine (943 mg) and 2-ethoxycarbonyl-malonic acid diethyl ester (3.15 mL) in a test tube was heated for 30 min at 170° C. and then 30 min at 200° C.; then cooled, the residue was directly column-purified to give the desired product (778 mg) as brown liquid. ESI (m/z): 279 (M+H)+.

Workup

  1. custom30 min
  2. customat 200° C.
  3. temperaturethen cooled
  4. customthe residue was directly column-purified

Sources & evidence

ORD record
ord-4c519e0819af4b33a7ff9120244e6e6e
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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