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 1062806ノート

反応式

HRID 1062806 の反応式
[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

参加物

5

反応物 3

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 22281927HCID 22281927、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-27dbaa5d04e64a2ebcc03c1611ad4e57
出典データセット
uspto-grants-2005_11
特許番号
US06962923B2

反応ノート

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