Dicyclohexylcarbodiimide → HCID 178481054, compound

HRID 1762802Notes

Reaction equation

HRID 1762802 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([F:18])[CH:17]=1)[CH2:5][N:6]1[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=[C:7]1[SH:14].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>O1CCCC1>[F:18][C:16]1[CH:15]=[C:4]([CH:3]=[C:2]([F:1])[CH:17]=1)[CH2:5][N:6]1[C:10]([C:11]([N:46]2[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]2)=[O:13])=[CH:9][N:8]=[C:7]1[SH:14]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 531671-Methylpiperazine2×HCID 80170N-HydroxysuccinimideHCID 178524783HCID 178524783, compound

Product 1

HCID 178481054HCID 178481054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(3,5-difluorobenzyl)-2-mercaptoimidazole-5-carboxylic acid (2.70 g, 0.01 moles) in tetrahydrofuran (25 ml) was added N-hydroxysuccinimide (1.27 g, 0.011 mole) followed by dropwise addition of dicyclohexylcarbodiimide (2.06 g, 0.01 mole) in tetrahydrofuran (30 ml). A solution of N-methylpiperazine (1.22 ml, 0.011 mole) in tetrahydrofuran (10 ml) was added and the mixture stirred at 25° C. for 2 hours and then at 40° C. for 16 hours. Additional N-methylpiperazine (1.0 ml, 0.009 mole) was added and the reaction mixture was stirred at 40° C. for 1.5 hours. The reaction mixture was filtered and the solvent removed under vacuum. The residue was dissolved in ethyl acetate and was washed with dilute sodium carbonate, water, and brine. The solution was dried and the solvent removed under vacuum. The resulting solid was triturated with ether and the product was filtered and dried to give a solid, m.p.: 243°-244° C. (2.10 g, 60%).

Workup

  1. waitat 40° C. for 16 hours
  2. stirringthe reaction mixture was stirred at 40° C. for 1.5 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent removed under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwas washed with dilute sodium carbonate, water, and brine
  7. customThe solution was dried
  8. customthe solvent removed under vacuum
  9. customThe resulting solid was triturated with ether
  10. filtrationthe product was filtered
  11. customdried
  12. customto give a solid, m.p.: 243°-244° C. (2.10 g, 60%)

Sources & evidence

ORD record
ord-bf1780712aa34d80a959796dd4c89a41
Source dataset
uspto-grants-1989_05
Patent number
US04835154

Reaction notes

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