Potassium Carbonate → HCID 21947691, compound

HRID 2214440Notes

Reaction equation

HRID 2214440 reaction equation
[CH3:1][S:2][C:3]1[NH:4][C:5]2[C:10](=[O:11])[N:9]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[N:8]=[CH:7][C:6]=2[N:23]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]#[C:33][CH3:34]>CN(C)C=O.O.[Cl-].[Na+]>[CH2:31]([N:4]1[C:5]2[C:10](=[O:11])[N:9]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[N:8]=[CH:7][C:6]=2[N:23]=[C:3]1[S:2][CH3:1])[C:32]#[C:33][CH3:34]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 178503361HCID 178503361, compound

Product 1

HCID 21947691HCID 21947691, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 900 mg (2.79 mmol) of 2-methylsulphanyl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (Example 1f) in 15 ml of dimethylformamide was combined with 415 mg (3.0 mmol) of potassium carbonate and 399 mg (3.0 mmol) of 1-bromo-2-butyne and stirred at ambient temperature for eight hours. Then the mixture was diluted with approx. 30 ml of water and saturated with sodium chloride, whereupon the reaction product crystallised out. It was suction filtered and purified by column chromatography (silica gel, eluant:petroleum ether with 10–50% ethyl acetate).

Workup

  1. customcrystallised out
  2. filtrationfiltered
  3. custompurified by column chromatography (silica gel, eluant:petroleum ether with 10–50% ethyl acetate)

Sources & evidence

ORD record
ord-939f5b426a204a0cbbf18523226aebe0
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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