Methylamine → HCID 22351064, compound

HRID 896504Notes

Reaction equation

HRID 896504 reaction equation
[C:1]([C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:34]=[CH:33][C:23]([CH2:24][CH:25]([C:29]([O:31][CH3:32])=[O:30])[C:26](O)=[O:27])=[CH:22][CH:21]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:41][NH2:42]>ClCCl>[C:1]([C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:34]=[CH:33][C:23]([CH2:24][CH:25]([C:26]([NH:42][CH3:41])=[O:27])[C:29]([O:31][CH3:32])=[O:30])=[CH:22][CH:21]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 16126775HCID 16126775, compound

Product 1

HCID 22351064HCID 22351064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained in Example 63 is dissolved in anhydrous dichloromethane and then 1.5 equivalents of thionyl chloride are added and the mixture is heated at reflux for 1 hour 30 minutes. The reaction mixture is then cooled using an ice bath, and 1.2 equivalents of methylamine are added via the top of the condenser. The reaction mixture is stirred for one hour and is then extracted with dichloromethane. The organic phases are washed with a sodium carbonate solution, and with water, and are then filtered, dried over magnesium sulphate and evaporated under reduced pressure. The resulting residue is purified by flash chromatography using an ethyl acetate/cyclohexane mixture as eluant. The resulting title product is recrystallised from a toluene/cyclohexane mixture.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1 hour 30 minutes
  3. temperatureThe reaction mixture is then cooled
  4. extractionis then extracted with dichloromethane
  5. washThe organic phases are washed with a sodium carbonate solution
  6. filtrationwith water, and are then filtered
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customThe resulting residue is purified by flash chromatography
  10. customThe resulting title product is recrystallised from a toluene/cyclohexane mixture

Sources & evidence

ORD record
ord-f6d16111375a417597ed465a071b5b23
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

Loading…