Dicyclohexylcarbodiimide → HCID 21650183, compound

HRID 1975608Notes

Reaction equation

HRID 1975608 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]([OH:10])=[O:9].[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[C:38][CH2:39]O)=[CH:33][CH:32]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[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:10][CH2:39][C:38]#[C:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][C:26]2[NH:27][CH:28]=[CH:29][N:25]=2)=[CH:36][CH:35]=1)=[O:9]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 70047405HCID 70047405, compound

Product 1

HCID 21650183HCID 21650183, 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 212 mg (1 mM) of 3-[4-(1-imidazolylmethyl)phenyl]-2-propyn-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 temperature, 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, whereby the captioned compound was obtained. The yield was 421 mg (80%).

Workup

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

Sources & evidence

ORD record
ord-c44c2358cc4041998b1495a86696a74c
Source dataset
uspto-grants-1994_02
Patent number
US05286869

Reaction notes

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