Methane → HCID 178432423, compound

HRID 2268745Notes

Reaction equation

HRID 2268745 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6](F)[NH:5][C:4]=2[CH:3]=1.Cl.[CH3:15][C:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.C>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6]([NH:22][C:16]3([CH3:15])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:5][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 3021577(1-Methylcyclohexyl)amine hydrochlorideHCID 109226916-Chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide

Product 1

HCID 178432423HCID 178432423, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (0.5 g, 2.08 mmol), 1-methylcyclohexylamine hydrochloride (373 mg, 2.49 mmol) and triethylamine (0.58 ml, 4.16 mmol) in ethanol (3 ml) was stirred for 20 h at 50° C. and then for 22 h at 100° C. in a sealed flask. The cooled mixture was concentrated in vacuo and the residue was triturated with water followed by adjustment to pH <2 with 4M hydrochloric acid. The crude product was isolated by filtration and dissolved in 1 N sodium hydroxide followed by treatment with decolourising charcoal. After filtration, the solution was acidified to pH <2 with 4M hydrochloric acid and the precipitate was filtered off and purified by chromatography (dichloromethane/methanol (19:1)). Recrystallisation from ethanol afforded 55 mg (8%) of the pure title compound; mp 218-219° C.; 1H-NMR (DMSO-d6): δ1.18-1.54 (m, 11H), 1.97-2.12 (m, 2H), 6.55 (br s, 1H), 7.12 (s, 1H), 10.60 (br s, 1H).

Workup

  1. waitfor 22 h at 100° C. in a sealed flask
  2. concentrationThe cooled mixture was concentrated in vacuo
  3. customthe residue was triturated with water
  4. customThe crude product was isolated by filtration
  5. filtrationAfter filtration
  6. filtrationthe precipitate was filtered off
  7. custompurified by chromatography (dichloromethane/methanol (19:1))
  8. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-722892babcab491890211558bc0a25b5
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

Loading…