2-Dimethylaminopyridine → ethyl 2-{4-[([4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-yl]amino)sulfonyl]phenyl}-2-methylpropanoate

HRID 1062761Notes

Reaction equation

HRID 1062761 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)=[N:12][N:13]([CH3:16])[C:14]=3[NH2:15])=[CH:9][C:4]=2[O:3][CH2:2]1.CN(C1C=CC=CN=1)C.Cl[S:32]([C:35]1[CH:40]=[CH:39][C:38]([C:41]([CH3:48])([CH3:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)=[N:12][N:13]([CH3:16])[C:14]=3[NH:15][S:32]([C:35]3[CH:36]=[CH:37][C:38]([C:41]([CH3:47])([CH3:48])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:39][CH:40]=3)(=[O:34])=[O:33])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 11055406Ethyl 2-[4-(chlorosulfonyl)phenyl]-2-methylpropanoateHCID 22281971HCID 22281971, compound

Product 1

HCID 22282041ethyl 2-{4-[([4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-yl]amino)sulfonyl]phenyl}-2-methylpropanoateYield 64.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-ylamine (Preparation 50) (230 mg) in anhydrous pyridine (8 ml) at room temperature under an atmosphere of nitrogen was added dimethylaminopyridine (108 mg) and ethyl 2-[4-(chlorosulfonyl)phenyl]-2-methylpropanoate (512 mg). The mixture was stirred overnight and then concentrated under reduced pressure. HCl 0.01N (100 ml) was poured on the resulting yellow syrup and the resulting mixture was extracted with dichloromethane (3×50 ml). The organic fraction was concentrated under reduced pressure and the residue was dissolved in methanol (8 ml). An aqueous solution of sodium hydroxyde (2M, 2 ml) was added and the reaction was stirred overnight. Water (10 ml) was then added, the mixture was acidified with an aqueous solution of HCl (1N) and extracted with dichloromethane (3×10 ml). The combined organic fractions were dried on sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 35 g) eluted with hexane:ethyl acetate (2:1) to yield the title as a pale yellow oil (281 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionHCl 0.01N (100 ml) was poured on the resulting yellow syrup
  3. extractionthe resulting mixture was extracted with dichloromethane (3×50 ml)
  4. concentrationThe organic fraction was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (8 ml)
  6. additionAn aqueous solution of sodium hydroxyde (2M, 2 ml) was added
  7. stirringthe reaction was stirred overnight
  8. additionWater (10 ml) was then added
  9. extractionextracted with dichloromethane (3×10 ml)
  10. customThe combined organic fractions were dried on sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography (silica, 35 g)
  13. washeluted with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2f8d17d8c91c4be8af7704aeda502c3b
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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