Guanidine Hydrochloride → HCID 136185985, compound

HRID 1589146Notes

Reaction equation

HRID 1589146 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23](=O)[CH2:24][C:25]([O:27]CC)=O)=[C:10]1[C:31]([O:33][CH2:34][CH3:35])=[O:32].N12CCCC1=NCCC2.Cl.[NH2:46][C:47]([NH2:49])=[NH:48]>C(O)C>[NH2:48][C:47]1[NH:49][C:25](=[O:27])[CH:24]=[C:23]([CH2:22][O:21][CH2:20][C:11]2[NH:12][C:13]([CH3:19])=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=3[Cl:1])[C:10]=2[C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:46]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 14547435HCID 14547435, compound

Product 1

HCID 136185985HCID 136185985, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetoacetate (0.74 g), 1,5-diazabicyclo[4.3.0]non-5-ene (0.25 g) and guanidine hydrochloride (0.14 g) in ethanol (30 ml) was heated under reflux for 5.5 hours and then evaporated. The residue was dissolved in chloroform and the solution washed successively with water, 10% aqueous sodium carbonate solution and water, dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with ethyl acetate and the resulting precipitate collected, washed thoroughly with diethyl ether, recrystallized from ethyl acetate/ethanol and dried to give the title compound (0.20 g), m.p. 222°-225° C. Found: C,52.10; H,4.56; N,10.54. C23H24Cl2N4O6 requires C,52.78; H,4.62; N,10.70%.

Workup

  1. temperatureunder reflux for 5.5 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution washed successively with water, 10% aqueous sodium carbonate solution and water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. customThe residue was triturated with ethyl acetate
  8. customthe resulting precipitate collected
  9. washwashed thoroughly with diethyl ether
  10. customrecrystallized from ethyl acetate/ethanol
  11. customdried

Sources & evidence

ORD record
ord-3731c45cefb24f0f8c7caa1245382449
Source dataset
uspto-grants-1986_02
Patent number
US04568677

Reaction notes

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