2-Methyl-2-thiopseudourea sulfate → HCID 13457210, compound

HRID 2290321Notes

Reaction equation

HRID 2290321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]([NH:24][NH2:25])=O)=[C:9]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].S(O)(O)(=O)=O.CS[C:38](=[NH:40])[NH2:39].N12CCCC1=NCCC2>C(O)CCC>[NH2:40][C:38]1[N:39]=[C:22]([CH2:21][O:20][CH2:19][C:10]2[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[NH:24][N:25]=1

Participants

5

Reactant 3

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 70044597HCID 70044597, compound

Product 1

HCID 13457210HCID 13457210, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}-acetylhydrazine (0.87 g), 2-methylisothiourea sulphate (0.68 g) and 1,5-diazabicyclo[4.3.0]non-5-ene (0.74 g) in n-butanol (30 ml) was heated under reflux for 16 hours and then evaporated. The residue was partitioned between dichloromethane and water and the organic layer dried (Na2SO4) and evaporated. The residual oil was purified by chromatography on silica (t.l.c. grade, 10 g) using dichloromethane plus 0-100% v/v ethyl acetate as eluant. Appropriate fractions were combined and evaporated and the residual oil triturated with ethyl acetate. The resulting solid was collected, washed with ethyl acetate and dried to give the title compound (0.14 g), m.p. 199°-202° C. decomp.

Workup

  1. temperatureunder reflux for 16 hours
  2. customevaporated
  3. customThe residue was partitioned between dichloromethane and water
  4. dry with materialthe organic layer dried (Na2SO4)
  5. customevaporated
  6. customThe residual oil was purified by chromatography on silica (t.l.c. grade, 10 g)
  7. customevaporated
  8. customthe residual oil triturated with ethyl acetate
  9. customThe resulting solid was collected
  10. washwashed with ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-cd84fbe6218545f09419eaf47065d42b
Source dataset
uspto-grants-1986_10
Patent number
US04616024

Reaction notes

Loading…