Tetrahydrofuran → HCID 68996099, 화합물

HRID 1180890노트

반응식

HRID 1180890 반응식
[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][NH:5][CH:6]=1.[CH3:23][C:24](C)([O-:26])[CH3:25].[K+].O1CC[CH2:31][CH2:30]1.O1CCCC1Br>CN(C)C=O>[Br:1][C:2]1[C:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])=[CH:9][CH:8]=2)=[N:4][N:5]([CH2:23][CH:24]2[CH2:25][CH2:31][CH2:30][O:26]2)[CH:6]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 130702942-BromotetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178521959HCID 178521959, 화합물

생성물 1

HCID 68996099HCID 68996099, 화합물수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-[4-(4-bromo-1H-pyrazol-3-yl)phenyl]-N′-phenylurea (0.28 mmol) in anhydrous N,N-dimethylformamide (6 mL) cooled to 0° C. was added 1.0M potassium tert-butoxide in tetrahydrofuran (1.12 mmol) dropwise. The reaction mixture was stirred for a further 15 minutes in the cold before dropwise addition of tetrahydrofuryl bromide (0.28 mmol). The reaction mixture was stirred at room temperature for 18 h, followed by quenching with saturated aqueous ammonium chloride (1 mL). The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Gilson reverse phase HPLC afforded the title compound (53%). ESMS [M+H]+: 441.4

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. customby quenching with saturated aqueous ammonium chloride (1 mL)
  3. additionThe reaction mixture was diluted with water (3 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-135aa5861a0941f6bd3888771aa50e95
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282588B2

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