Triethylamine → 2-{4-[(5,5-Dioxido-2,3-dihydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}-n'-hydroxyethanimidamide

HRID 851898Notes

Reaction equation

HRID 851898 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][OH:10].[O:11]=[S:12]1(=[O:35])[C:17]2[CH:18]=[C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]#[N:31])=[CH:25][CH:24]=3)[CH:20]=[CH:21][C:16]=2[N:15]2[CH2:32][CH2:33][CH2:34][CH:14]2[NH:13]1>CS(C)=O>[O:35]=[S:12]1(=[O:11])[C:17]2[CH:18]=[C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30](=[N:9][OH:10])[NH2:31])=[CH:25][CH:24]=3)[CH:20]=[CH:21][C:16]=2[N:15]2[CH2:32][CH2:33][CH2:34][C:14]2=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 69199240{4-[(5,5-Dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}acetonitrile

Product 1

HCID 878716182-{4-[(5,5-Dioxido-2,3-dihydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl}-n'-hydroxyethanimidamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.51 ml (18.0 mmol) of triethylamine are added to a solution of 1.25 g (18.0 mmol) of hydroxylamine hydrochloride in 4 ml of DMSO and the suspension is stirred for 10 minutes. The precipitate is filtered off and the filtrate is concentrated. 992 mg (3.00 mmol) of the product of Step A of Example 27 are added to the filtrate and the solution is stirred at 75° C. for 1 hour 30 minutes. The solution is allowed to return to ambient temperature, and precipitation of the reaction mixture is brought about using water. The precipitate is filtered off to yield the title product.

Workup

  1. filtrationThe precipitate is filtered off
  2. concentrationthe filtrate is concentrated
  3. stirringthe solution is stirred at 75° C. for 1 hour 30 minutes
  4. customto return to ambient temperature
  5. customprecipitation of the reaction mixture
  6. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-baace91d42e7404c859bed8af6fb546b
Source dataset
uspto-grants-2007_08
Patent number
US07253162B2

Reaction notes

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