Triethylamine → HCID 22609231, compound

HRID 2306575Notes

Reaction equation

HRID 2306575 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:13][N:14]=[C:7]1[N:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:5]2=[O:27].C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH2:20]([N:6]1[C:5](=[O:27])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([N:1]([S:36]([CH3:35])(=[O:38])=[O:37])[S:36]([CH3:35])(=[O:38])=[O:37])[CH:3]=2)[N:8]2[C:12]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)=[N:13][N:14]=[C:7]12)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22609256HCID 22609256, compound

Product 1

HCID 22609231HCID 22609231, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 20 ml balloon flask, we resuspend 0.55 g (1.5 mmol) of 7-amino-4-benzyl-1-(pyrrolidin-1-yl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (described in example 225) in 10 ml methylene chloride. We add 0.42 ml (3.0 mmol) of triethylamine then 0.24 ml (3.0 mmol) of methanesulfonyl chloride. The obtained solution is shaken for 24 hours at ambient temperature. After cooling down, the obtained solution is washed in water, dried on Na2SO4 then evaporated under vacuum. The crude mixture of the 2 obtained compounds (0.85 g) is chromatographied on silica column by elution with the mixture CH2Cl2 99/CH3OH 1/NH4OH 0.1. The fractions containing the first product by elution order are joined and evaporated under vacuum to give 0.65 g of 4-benzyl-7-(N,N-dimethylsulfonylamino)-1-(pyrrolidin-1-yl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one.

Workup

  1. customIn a 20 ml balloon flask, we resuspend
  2. temperatureAfter cooling down
  3. washthe obtained solution is washed in water
  4. customdried on Na2SO4
  5. customthen evaporated under vacuum
  6. additionThe crude mixture of the 2 obtained compounds (0.85 g)
  7. washis chromatographied on silica column by elution with the mixture CH2Cl2 99/CH3OH 1/NH4OH 0.1
  8. additionThe fractions containing the first product
  9. washby elution order
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-4353141cf3694d8c847a9ec04bbbcb5b
Source dataset
uspto-grants-2004_12
Patent number
US06828315B1

Reaction notes

Loading…