Water → HCID 69519722, compound

HRID 1179879Notes

Reaction equation

HRID 1179879 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-90fa680bb6e1493ebf6eb25e83474498
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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