Triethylamine → HCID 86604719, compound

HRID 915739Notes

Reaction equation

HRID 915739 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][OH:10].[F:11][CH2:12][CH2:13][N:14]1[C:19]2[CH:20]=[CH:21][C:22]([O:24][C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])=[CH:23][C:18]=2[S:17](=[O:34])(=[O:33])[N:16]=[CH:15]1>CS(C)=O>[F:11][CH2:12][CH2:13][N:14]1[C:19]2[CH:20]=[CH:21][C:22]([O:24][C:25]3[CH:26]=[C:27]([C:28](=[N:9][OH:10])[NH2:29])[CH:30]=[CH:31][CH:32]=3)=[CH:23][C:18]=2[S:17](=[O:33])(=[O:34])[N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 87840440HCID 87840440, compound

Product 1

HCID 86604719HCID 86604719, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

770 μL (5.52 mmol) of triethylamine are added to a solution of hydroxylamine hydrochloride (384 mg, 5.52 mmol) in 1.8 ml of DMSO, and the suspension is stirred for 20 minutes at ambient temperature. The precipitate is filtered off and the filtrate is concentrated in vacuo. To the resulting filtrate there are added 225 mg (0.921 mmol) of the compound of Step A above and the solution is stirred at 75° C. for 4 hours. The reaction mixture is cooled to ambient temperature and the reaction mixture is precipitated from water. A white, non-filterable, gummy paste is obtained which is separated from the aqueous phase by simple decanting. The gum is triturated in ethanol until crystallisation occurs. The solid is filtered off to yield the title compound.

Workup

  1. filtrationThe precipitate is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. stirringthe solution is stirred at 75° C. for 4 hours
  4. temperatureThe reaction mixture is cooled to ambient temperature
  5. customthe reaction mixture is precipitated from water
  6. customA white, non-filterable, gummy paste is obtained which
  7. customis separated from the aqueous phase by simple decanting
  8. customThe gum is triturated in ethanol until crystallisation
  9. filtrationThe solid is filtered off

Sources & evidence

ORD record
ord-9209a028860048ea8bb005a9ce38c81e
Source dataset
uspto-grants-2007_09
Patent number
US07268130B2

Reaction notes

Loading…