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Water → 1'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]spiro[1-benzofuran-3,4'-piperidine]

HRID 2036084
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HRID 2036084 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.[NH:14]1[CH2:19][CH2:18][C:17]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][CH2:20]2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:14]3[CH2:19][CH2:18][C:17]4([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[O:21][CH2:20]4)[CH2:16][CH2:15]3)=[CH:7][CH:6]=2)[S:12][N:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 109218293-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazineHCID 151870462H-Spiro(1-benzofuran-3,4'-piperidine)

생성물 1

HCID 250006571'-[6-(3-Methyl-1,2,4-thiadiazol-5-yl)pyridazin-3-yl]spiro[1-benzofuran-3,4'-piperidine]수율 35.4%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A solution (4 ml) of 3-Chloro-6-(3-methyl-1,2,4-thiadiazol-5-yl)pyridazine (69 mg), spiro[1-benzofuran-3,4′-piperidine] (62 mg) and potassium carbonate (54 mg) in N,N-dimethylformamide was stirred at 70° C. overnight. After cooling to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated. The residue was purified by silica gel chromatography (33% ethyl acetate/hexane) to give the object product (42 mg, 35%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel chromatography (33% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f7bb8bc700d842668f9c51a7bd3eb42b
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575167B2

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