N,N-Dimethylethylenediamine → HCID 17782371, compound

HRID 636390Notes

Reaction equation

HRID 636390 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[C:7]1([S:13]([C:16]2[C:17]([S:27][CH3:28])=[N:18][N:19]3[C:24](Cl)=[CH:23][C:22]([CH3:26])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[C:7]1([S:13]([C:16]2[C:17]([S:27][CH3:28])=[N:18][N:19]3[C:24]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:23][C:22]([CH3:26])=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 109810973-Benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 17782371HCID 17782371, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.088 g (1 mmol) of 2-dimethylaminoethylamine was added to a solution of 0.17 g (0.5 mmol) of 3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine in 3 ml of DMF and stirred at 60° for 2 hrs. The reaction solution was cooled to RT and evaporated in a high vacuum. The residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2, and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 19:1) and crystallization from EtOH yielded 0.23 g (73%) of N-(3-benzenesulphonyl-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-yl)-N′,N′-dimethyl-ethane-1,2-diamine as colorless crystals, m.p. 190-191°.

Workup

  1. customevaporated in a high vacuum
  2. customThe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 19:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-4e678bd16a664ac48a020329b6d10d70
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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