Dimethylformamide → HCID 23503671, compound

HRID 1835447Notes

Reaction equation

HRID 1835447 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][C:31]([C:34]2[CH:35]=[C:36]([NH2:40])[CH:37]=[CH:38][CH:39]=2)=[CH:30][N:29]=1>ClCCl.N1C=CC=CC=1>[N:28]1[CH:33]=[CH:32][C:31]([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)=[CH:30][N:29]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 80468Fluorene-1-carboxylic acidHCID 13634839HCID 13634839, compound

Product 1

HCID 23503671HCID 23503671, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a suspension of 1-fluorenecarboxylic acid (120 mg) and oxalyl chloride (0.12 ml) in dichloromethane (2.5 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-4-yl)phenylamine (98 mg) and pyridine (0.14 ml) in dichloromethane (2 ml) was dropwise added a solution of the acid chloride obtained above in dichloromethane (5 ml), and the mixture was stirred 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-4-yl)-phenyl)-9H-fluorene-1-carboxamide (133 mg, 63.9%)

Workup

  1. customThe resultant solution was evaporated
  2. customto give a crude acid chloride
  3. stirringthe mixture was stirred 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-d8abe5b339ba4cc29ca18cb1191b97d9
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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