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

HRID 1368615Notes

Reaction equation

HRID 1368615 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-d4044a5b4a074d27aa213bcce0d5457f
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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