Dimethylformamide → HCID 23503691, compound

HRID 1835440Notes

Reaction equation

HRID 1835440 reaction equation
[C:1]1([C:14](O)=[O:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]2[CH:35]=[C:36]([NH2:40])[CH:37]=[CH:38][CH:39]=2)[N:29]=1>ClCCl.N1C=CC=CC=1>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]2[CH:35]=[C:36]([NH:40][C:14]([C:1]3[C:13]4[CH2:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]=4[CH:4]=[CH:3][CH:2]=3)=[O:15])[CH:37]=[CH:38][CH:39]=2)[N:29]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 80468Fluorene-1-carboxylic acidHCID 136348303-(Pyridazin-3-yl)aniline

Product 1

HCID 23503691HCID 23503691, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a suspension of 1-fluorenecarboxylic acid (184 mg) and oxalyl chloride (0.2 ml) in dichloromethane (4 ml) was added N,N-dimethylformamide (0.01 ml), and the mixture was stirred for 2 hours. The resultant solution was evaporated to give a crude acid chloride. To a suspension of 3-pyridazin-3-yl-phenylamine (150 mg) and pyridine (0.21 ml) in dichloromethane (2 ml) was dropwise added a solution of the acid chloride obtained above in dichloromethane. (5 ml) followed by stirring for an hour. The mixture was diluted with dichloromethane and washed with an aqueous solution of sodium hydrogen carbonate and brine. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(3-(pyridazin-3-yl)phenyl)-9H-fluorene-1-carboxamide (44 mg, 13.8%).

Workup

  1. customThe resultant solution was evaporated
  2. customto give a crude acid chloride
  3. stirringby stirring for an hour
  4. washwashed with an aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialThe separated organic layer was dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by a silica gel column chromatography
  8. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-5bc2e499036146268b4b8433f634929f
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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