Water → HCID 69519722, compound

HRID 1831255Notes

Reaction equation

HRID 1831255 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[N:13]=[N:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH3:15][N:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17](Cl)=[O:18].N12CCN(CC1)C[CH2:27]2.O.CN(C)[CH:37]=[O:38]>>[CH3:37][O:38][C:5]1[CH:6]=[CH:27][C:2]([CH2:7][C:8]2[N:13]=[N:12][C:11]([O:14][C:17](=[O:18])[N:16]([CH3:15])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:10][CH:9]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178515972HCID 178515972, compound

Product 1

HCID 69519722HCID 69519722, compoundYield 41%

Procedure

A solution of 6-(2-pyridinylmethyl)-3-pyridazinol (97 mg, 0.45 mmol), N-methyl-N-phenylcarbamoyl chloride (76 mg, 0.45 mmol) and 1,4-diazabicyclo[2.2.2]octane (50 mg, 0.45 mmol) in dimethylformamide (10 ml) was stirred at room temperature for 2 hours. Water was added and the solution was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (50:50)) yielding the title compound (117 mg, 41% yield) as a white solid.

Workup

  1. extractionthe solution was extracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (50:50))

Sources & evidence

ORD record
ord-eec099c4254a4e988133a62ca50611db
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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