2-Furancarboxylic acid → HCID 19780218, compound

HRID 2081572Notes

Reaction equation

HRID 2081572 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:10]3[CH2:20][CH2:21][CH2:22][C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](O)=[O:29].Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:10]3[CH2:20][CH2:21][CH2:22][C:9]=3[N:8]=2)[CH2:6][CH2:5]1)=[O:29]

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9839237HCID 9839237, compound

Product 1

HCID 19780218HCID 19780218, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-(1-piperazinyl)-4-(4-fluorophenyl)-6,7-dihydro-5H-cyclopentapyrimidine (1.0 g), 2-furoic acid (0.38 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.79 g) and chloroform (40 ml) is stirred at room temperature for 2 hours. The reaction mixture is washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The residue is dissolved in toluene, and the solution is subjected to silica gel column chromatography. The fractions eluted with toluene-ethyl acetate (9:1) are collected, and the product therefrom is recrystallized from ethanol to give the desired compound (0.62 g), m.p. 124°-125° C. (ethanol).

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in toluene
  5. washThe fractions eluted with toluene-ethyl acetate (9:1)
  6. customare collected
  7. customthe product therefrom is recrystallized from ethanol

Sources & evidence

ORD record
ord-de39681b15ad4eaa90e368686cfd816a
Source dataset
uspto-grants-1993_02
Patent number
US05185338

Reaction notes

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