Dicyclohexylcarbodiimide → HCID 14877542, compound

HRID 1975593Notes

Reaction equation

HRID 1975593 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8](O)=[O:9].[N:25]1([CH2:30][C:31]2[CH:36]=[CH:35][C:34](/[CH:37]=[CH:38]/[CH2:39][OH:40])=[CH:33][CH:32]=2)[CH:29]=[N:28][CH:27]=[N:26]1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH3:24][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:40][CH2:39]/[CH:38]=[CH:37]/[C:34]2[CH:35]=[CH:36][C:31]([CH2:30][N:25]3[CH:29]=[N:28][CH:27]=[N:26]3)=[CH:32][CH:33]=2)=[O:9])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 19100107HCID 19100107, compound

Product 1

HCID 14877542HCID 14877542, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

332 mg (1 mM) of 1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid together with 215 mg (1 mM) of (E)-3-{4-(1,2,4-triazol-1-yl-methyl)phenyl}-2-propen-1-ol, 248 mg (1.2 mM) of dicyclohexylcarbodiimide and 134 mg (1.1 MM) of 4-N,N-dimethylaminopyridine were dissolved in 5 ml of toluene, while heating, and refluxed for six hours. The solution was cooled to room temperatures, and the crystals produced were filtered off. The filtrate was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled away, the residue was purified by chromatography on a silica gel column, the captioned compound was obtained. The yield was 522 mg (98.6%).

Workup

  1. temperaturewhile heating
  2. temperaturerefluxed for six hours
  3. temperatureThe solution was cooled to room temperatures
  4. customthe crystals produced
  5. filtrationwere filtered off
  6. washThe filtrate was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled away
  9. customthe residue was purified by chromatography on a silica gel column
  10. customthe captioned compound was obtained

Sources & evidence

ORD record
ord-6f3a82477bc84823aabbbd14cc5147fe
Source dataset
uspto-grants-1994_02
Patent number
US05286869

Reaction notes

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