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

HRID 1062806Notes

Reaction equation

HRID 1062806 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[C:16]([O:22][CH2:23][CH2:24][O:25][C:26]4[N:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=4)=[N:17][N:18]([CH3:21])[C:19]=3[NH2:20])=[CH:14][C:9]=2[O:8][CH2:7]1.CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[C:16]([O:22][CH2:23][CH2:24][O:25][C:26]4[N:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=4)=[N:17][N:18]([CH3:21])[C:19]=3[N:20]([S:2]([CH3:1])(=[O:4])=[O:3])[S:2]([CH3:1])(=[O:4])=[O:3])=[CH:14][C:9]=2[O:8][CH2:7]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 22281927HCID 22281927, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (20 ul) was added at room temperature under an atmosphere of nitrogen to a mixture of 4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-ylamine (50 mg) (Preparation 48), dimethylaminopyridine (16 mg) in anhydrous pyridine (2.4 ml) and the reaction was stirred for 24 h. The mixture was concentrated under reduced pressure, then a saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml), and brine (6 ml) were sequentially added to the residue. The aqueous phase was extracted with ethyl acetate (2×8 ml) and the combined organic fractions were washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The oil was purified by preparative TLC (silica) eluted with dichloromethane:methanol (95:5) to yield the title compound as a pale yellow oil (71 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiona saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml), and brine (6 ml) were sequentially added to the residue
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×8 ml)
  4. washthe combined organic fractions were washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe oil was purified by preparative TLC (silica)
  8. washeluted with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-27dbaa5d04e64a2ebcc03c1611ad4e57
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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