Triethylamine → 3-{1-[1-(2,2,3,3,4,4,4-Heptafluoro-butyl)-piperidin-4-yl]-indol-3-yl}-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione

HRID 1077951노트

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HRID 1077951 반응식
[F:1][C:2]([F:26])([F:25])[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1.[C:27](Cl)(=[O:31])[C:28](Cl)=O.Cl.[C:34](=[NH:37])([OH:36])[CH3:35].[CH2:38]([N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])C.O.[C:46]1(C)[CH:51]=CC(S(O)(=O)=O)=[CH:48][CH:47]=1>CCOCC.C(Cl)Cl>[F:22][C:4]([F:21])([C:3]([F:23])([F:24])[C:2]([F:1])([F:25])[F:26])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:35]3[C:34](=[O:36])[NH:37][C:27](=[O:31])[C:28]=3[C:42]3[C:44]4[C:43](=[CH:51][CH:46]=[CH:47][CH:48]=4)[N:40]([CH3:38])[CH:41]=3)=[CH:13]2)[CH2:8][CH2:7]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 229072781-(4,4,4,3,3,2,2-Heptafluorobutyl)-4-(1-indolyl)-piperidineHCID 178465697HCID 178465697, 화합물

생성물 1

HCID 229072823-{1-[1-(2,2,3,3,4,4,4-Heptafluoro-butyl)-piperidin-4-yl]-indol-3-yl}-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a stirred 0° C. solution of 1-(4,4,4,3,3,2,2-heptafluorobutyl)-4-(1-indolyl)-piperidine (430 mg, 1.12 mmol) in dry ether (5 mL) was added oxalyl chloride (0.11 mL, 1.23 mmol). After 1 hour at room temperature, a yellow precipitate formed. The precipitant was collected by filtration under Ar, washed with ether, suspended in dry methylene chloride (10 mL) and treated with isopropyl(1-methyl)indol-3-yl)acetimidate hydrochloride (300 mg, 1.12 mmol). To this suspension was added triethylamine (0.78 mL, 5.6 mmol) in dry methylene chloride (3 mL) at 0° C. The reaction was stirred at ambient temperature for 3 hours and treated with p-toluene sulfonic acid monohydrate (slightly exothermic) (0.86 g, 4.5 mmol). After 30 minutes, the reaction was carefully quenched with saturated aqueous sodium hydrogen carbonate solution (30 mL). The organic phase was separated, washed with saturated aqueous sodium hydrogen carbonate solution, water, brine, dried, and evaporated. The residue was crystallized from an ethereal solution. Yield: 260 mg of bright orange crystals (38% of theory). H.Pt.: 231°-234° C.

후처리

  1. customa yellow precipitate formed
  2. filtrationThe precipitant was collected by filtration under Ar
  3. washwashed with ether
  4. waitAfter 30 minutes
  5. customthe reaction was carefully quenched with saturated aqueous sodium hydrogen carbonate solution (30 mL)
  6. customThe organic phase was separated
  7. washwashed with saturated aqueous sodium hydrogen carbonate solution, water, brine
  8. customdried
  9. customevaporated
  10. customThe residue was crystallized from an ethereal solution
  11. custom231°-234° C.

출처 및 근거

ORD 기록
ord-23c92ee79ff040fbbec3000dac3d6686
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05545636

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