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Dimethylformamide → HCID 57940624, compound

HRID 1437310
Notes
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Reaction equation

HRID 1437310 reaction equation
FC(F)(F)S(O)(=O)=O.[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:20][C:19]([C:28]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][NH:31]3)=[O:29])=[N:18]2)=[CH:13][CH:12]=1.CN(C)[CH:38]=[O:39]>CN(C)C1C=CN=CC=1>[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14]([N:17]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:20][C:19]([C:28]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][N:31]3[CH:38]=[O:39])=[O:29])=[N:18]2)=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 62406Trifluoromethanesulfonic acidHCID 11674985HCID 11674985, compound

Product 1

HCID 57940624HCID 57940624, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Dimethylaminopyridine (0.142 g) and trifluoromethane sulfonic acid anhydrate (0.140 mL) were added to 1-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]hexahydropyridazine (0.203 g) obtained in Example 162 in N,N-dimethylformamide (4.0 mL) at 0° C., followed by stirring for 20 minutes. The reaction mixture was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate. The organic layer was washed with saturated brine, and then dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (65.5 mg, 30%).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate anhydrate
  4. filtrationThe mixture was subjected to filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-7c6fd56dbd724b50b735bbc682be22d3
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622471B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes