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

HRID 1062760노트

반응식

HRID 1062760 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([S:7](Cl)(=[O:9])=[O:8])[N:4]=[CH:3]1.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[C:21]([O:27][CH2:28][CH2:29][O:30][C:31]4[N:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=4)=[N:22][N:23]([CH3:26])[C:24]=3[NH2:25])=[CH:19][C:14]=2[O:13][CH2:12]1.CN(C1C=CC=CN=1)C.N1C=C(S(N)(=O)=O)N=C1>N1C=CC=CC=1>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[C:21]([O:27][CH2:28][CH2:29][O:30][C:31]4[N:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=4)=[N:22][N:23]([CH3:26])[C:24]=3[NH:25][S:7]([C:5]3[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=3)(=[O:9])=[O:8])=[CH:19][C:14]=2[O:13][CH2:12]1

참가 물질

6

반응물 4

HCID 218852-DimethylaminopyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 22281927HCID 22281927, 화합물HCID 1785147611H-imidazole-4-sulfonamide

생성물 1

HCID 9871777N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

1-Methyl-1H-imidazole-4-sulfonyl chloride (45 mg) was carefully added at room temperature under an atmosphere of nitrogen to a solution of 4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-ylamine (Preparation 48) (50 mg) and dimethylaminopyridine (16 mg) in anhydrous pyridine (2.4 ml). The reaction was stirred for two days, then the mixture was concentrated under reduced pressure and a saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml) and brine (6 ml) were sequentially added. The aqueous phase was extracted with ethyl acetate (2×8 ml) and the combined organic phases were washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The black residue was purified by preparative TLC (silica) eluted with dichloromethane:methanol (95:5) yielding a mixture of title compound and N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-N-[(1-methyl-1H-imidazol-4-yl)sulfonyl)]-1H-imidazole-4-sulfonamide. The title compound was purified by HPLC (5.4 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
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×8 ml)
  4. washthe combined organic phases were washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe black residue was purified by preparative TLC (silica)
  8. washeluted with dichloromethane:methanol (95:5)
  9. customyielding

출처 및 근거

ORD 기록
ord-95b17707e34e4bb5b89bae5582a1d8bb
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

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