Methanol → HCID 70393667, compound

HRID 2291342Notes

Reaction equation

HRID 2291342 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][N:4]=[C:5]([NH2:22])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[NH:21])[O:19]C)[N:8]=1.C[NH:26][CH2:27][CH:28]([O:32]CC)[O:29]CC.[CH3:35][OH:36]>>[C:18]([OH:19])(=[O:36])/[CH:17]=[CH:27]\[C:28]([OH:29])=[O:32].[CH3:35][N:21]1[CH:28]=[CH:27][N:26]=[C:18]1[CH2:17][CH2:16][CH2:15][CH2:14][S:13][C:9]1[N:8]=[C:7]([NH:6][C:5]([NH2:22])=[N:4][CH2:3][C:2]([F:24])([F:23])[F:1])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 88646Ethanamine, 2,2-diethoxy-N-methyl-HCID 21279828HCID 21279828, compound

Product 1

HCID 70393667HCID 70393667, compound

Procedure

A solution of methyl 5-[2-(2-[2,2,2-trifluoroethyl]guanidino)pyrid-6-ylthio]valerimidate (0.3 g.) and N-methyl-2,2-diethoxyethylamine (0.44 g.) in MeOH (3 ml.) was kept at room temperature for 48 hours and then evaporated to dryness. The residue was dissolved in concentrated aqueous HCl and the solution heated at 90° for 30 minutes and then evaporated to dryness. The residue was partitioned between H2O and EtOAc and the aqueous phase basified with 10N NaOH and then extracted with EtOAc. The EtOAc extract was dried and evaporated to dryness and the residue dissolved in acetone. This solution was added to a solution of maleic acid in acetone, and the precipitate (0.12 g.) was collected and crystallised from EtOH to give 1-methyl-2-[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]pyrid-6-ylthio)butyl]imidazole hydrogen maleate, m.p. 107°-110°.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in concentrated aqueous HCl
  3. temperaturethe solution heated at 90° for 30 minutes
  4. customevaporated to dryness
  5. customThe residue was partitioned between H2O and EtOAc
  6. extractionextracted with EtOAc
  7. extractionThe EtOAc extract
  8. customwas dried
  9. customevaporated to dryness
  10. dissolutionthe residue dissolved in acetone
  11. additionThis solution was added to a solution of maleic acid in acetone
  12. customthe precipitate (0.12 g.) was collected
  13. customcrystallised from EtOH

Sources & evidence

ORD record
ord-d6d3b7c148704856871034dbb56dc1d6
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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