Tetrahydrofuran → HCID 58926034, 화합물

HRID 333376

반응식

HRID 333376 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3/[CH:13]=[C:14]([C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[C:15]([CH3:18])([CH3:17])[O:16]/3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N:27]1([CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C([BH3-])#N.[Na+].C1COCC1.C([O-])(O)=O.[Na+]>CN(C=O)C.CO.O.CC(O)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3\[O:16][C:15]([CH3:18])([CH3:17])[C:14]([C:19]4[CH:20]=[CH:21][C:22]([CH2:23][N:30]5[CH2:31][CH2:32][N:27]([CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])[CH2:28][CH2:29]5)=[CH:25][CH:26]=4)=[CH:13]\3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

참가 물질

10

반응물 5

HCID 8028TetrahydrofuranHCID 1394361-[2-(2-Hydroxyethoxy)ethyl]piperazineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 589264404-[(5E)-5-(6-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2,2-dimethyl-2,5-dihydrofuran-3-yl]benzaldehyde

생성물 1

HCID 58926034HCID 58926034, 화합물

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-[(5E)-5-(6-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2,2-dimethyl-2,5-dihydrofuran-3-yl]benzaldehyde (55 mg, 0.16 mmol), 2-(2-(piperazin-1-yl)ethoxy)ethanol (56 mg, 0.32 mmol) and 4 Å molecular sieves (100 mg) in anhydrous DMF (3 mL) was stirred at room temp for 16 hours. To this stirred mixture was added AcOH (10 mg), 1M sodium cyanoborohydride in THF solution (0.32 mL, 0.32 mmol) and 3 mL of anhydrous methanol. The reaction mixture was stirred at room temp for 5 hours and poured into 100 mL of water. Saturated NaHCO3 solution was then added until pH=9. The precipitates were filtered, washed with water, and dried in vacuo to give the crude product, which was purified through silica gel column with 5-10% MeOH/CHCl3 to give (3E)-6-fluoro-3-{4-[4-({4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}methyl)phenyl]-5,5-dimethylfuran-2(5H)-ylidene}-1,3-dihydro-2H-indol-2-one as yellow solid. Yield: 45 mg, 56%.

후처리

  1. stirringThe reaction mixture was stirred at room temp for 5 hours
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customto give the crude product, which
  6. customwas purified through silica gel column with 5-10% MeOH/CHCl3

출처 및 근거

ORD 기록
ord-313e3ce030ae4976abb29bea06cf4e77
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877923B2

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