Sodium → N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)methanesulfonamide

HRID 1062759Notes

Reaction equation

HRID 1062759 reaction equation
[Na].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([O:26][CH2:27][CH2:28][O:29][C:30]4[N:35]=[CH:34][C:33]([Cl:36])=[CH:32][N:31]=4)=[N:13][N:14]([CH3:25])[C:15]=3[N:16](S(C)(=O)=O)[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:10][C:5]=2[O:4][CH2:3]1>CO.ClCCl.[Cl-].[NH4+]>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([O:26][CH2:27][CH2:28][O:29][C:30]4[N:35]=[CH:34][C:33]([Cl:36])=[CH:32][N:31]=4)=[N:13][N:14]([CH3:25])[C:15]=3[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

6

Reactant 2

HCID 5360545SodiumHCID 22281925N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 22281900N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)methanesulfonamideYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

An aqueous solution of sodium hydroxyde (1M, 0.91 ml) was added at room temperature to a solution of N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-N-(methylsulfonyl)methane sulfonamide (Preparation 49) (50 mg) in a mixture of methanol (1 ml) and dichloromethane (0.3 ml). After 1 h the reaction was diluted with an aqueous saturated solution of ammonium chloride (4 ml) and the mixture was extracted with dichloromethane (3*5 ml). The combined organic fractions were dried over sodium sulfate and concentrated under reduced pressure. The pale yellow oil was purified by preparative TLC (silica) eluted with dichloromethane:methanol (95:5) to yield the title compound as a colourless oil (33 mg)

Workup

  1. extractionthe mixture was extracted with dichloromethane (3*5 ml)
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe pale yellow oil was purified by preparative TLC (silica)
  5. washeluted with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-20226d44fc0a4c0a9a4c88dc1b65e3a3
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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