Fluorene-1-carboxylic acid → N-[3-(4-methylimidazol-1-yl)-phenyl]-9H-fluorene-1-carboxamide

HRID 1835478Notes

Reaction equation

HRID 1835478 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.[CH3:17][C:18]1[N:19]=[CH:20][N:21]([C:23]2[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH2:26])[CH:22]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:17][C:18]1[N:19]=[CH:20][N:21]([C:23]2[CH:24]=[C:25]([NH:26][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:27]=[CH:28][CH:29]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 80468Fluorene-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 150301673-(4-Methyl-1H-imidazol-1-yl)benzenamine

Product 1

HCID 23503664N-[3-(4-methylimidazol-1-yl)-phenyl]-9H-fluorene-1-carboxamideYield 29.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 9H-fluorene-1-carboxylic acid (79 mg) and 3-(4-methylimidazol-1-yl)aniline (65 mg) in dichloromethane (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (101 mg) and 4-dimethylaminopyridine (23 mg), and the mire was stirred for 24 hours. The mix e was diluted with dichloromethane, washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with methanol, and the insoluble material was collected by filtration and dried to give N-[3-(4-methylimidazol-1-yl)-phenyl]-9H-fluorene-1-carboxamide (40 mg, 29.2%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe mixture was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with methanol
  5. filtrationthe insoluble material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a3964420ca4446a18820d0e500b517fb
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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