Potassium Carbonate → N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide

HRID 1960512노트

반응식

HRID 1960512 반응식
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]2[S:12][C:11]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][C:16]=4[NH:22][S:23]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)(=[O:25])=[O:24])=[N:10][CH2:9]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:37][CH:38]([F:40])I>CN(C)C=O.C(OCC)(=O)C>[F:37][CH:38]([F:40])[N:22]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[NH:14][C:13]([C:11]1[S:12][CH:8]([CH2:7][N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[CH2:9][N:10]=1)=[CH:21]2)[S:23]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[O:25]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2775155Difluoro(iodo)methaneHCID 59135769N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide

생성물 1

HCID 24899516N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide수율 27.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (200 mg) in N,N-dimethylformamide (3 mL) were added potassium carbonate (90.0 mg) and difluoroiodomethane (77.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (60 mg, yield 27%) as white crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS:513(MH+). melting point 185-186° C.

후처리

  1. washwashed with water and saturated brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b2ca271f34db42afb2cf13e632fd6f5e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410087B2

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