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 1062806노트

반응식

HRID 1062806 반응식
[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

참가 물질

5

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-27dbaa5d04e64a2ebcc03c1611ad4e57
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

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