p-Toluenesulfonic acid → 1-{[4-(2,3-Dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methyl-3-(1,2,4-triazol-4-yl)propane

HRID 569588Notes

Reaction equation

HRID 569588 reaction equation
[NH2:1][CH2:2][C:3]([OH:32])([CH3:31])[CH2:4][O:5][CH2:6][C:7]1[NH:8][C:9]([CH3:30])=[C:10]([C:26]([O:28][CH3:29])=[O:27])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[Cl:25])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].CN(C)/[CH:35]=[N:36]/[N:37]=[CH:38]/N(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:25][C:19]1[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=1[CH:11]1[C:10]([C:26]([O:28][CH3:29])=[O:27])=[C:9]([CH3:30])[NH:8][C:7]([CH2:6][O:5][CH2:4][C:3]([OH:32])([CH3:31])[CH2:2][N:1]2[CH:38]=[N:37][N:36]=[CH:35]2)=[C:12]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9613942N'-((Dimethylamino)methylene)-N,N-dimethylformohydrazonamideHCID 148106031-Amino-3-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methylpropane

Product 1

HCID 148106011-{[4-(2,3-Dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methyl-3-(1,2,4-triazol-4-yl)propaneYield 65.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-amino-3-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-hydroxy-2-methylpropane (0.25 g), N,N-dimethylformamide azine (0.21 g) and para-toluenesulphonic acid (10 mg) in toluene (10 ml) was heated under reflux for 1.5 hours and then partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with water, dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (5 g) using dichloromethane plus 0-5% methanol as the eluant. Appropriate fractions were combined and evaporated and the residue triturated with ether. The resulting solid was collected, washed with ether and dried to give the title compound (0.18 g), m.p. 172°-176° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. custompartitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by chromatography on SiO2 (5 g)
  8. customevaporated
  9. customthe residue triturated with ether
  10. customThe resulting solid was collected
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-aee10c1f14654c45b3f23998ceb80af7
Source dataset
uspto-grants-1988_03
Patent number
US04732985

Reaction notes

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