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 1378534ノート

反応式

HRID 1378534 の反応式
[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

参加物

8

反応物 5

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

生成物 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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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). M.Pt.: 231°-234° C.

後処理

  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

出典と根拠

ORDレコード
ord-0eb968f633af4debacd370bf5ab796fc
出典データセット
uspto-grants-1997_09
特許番号
US05668152

反応ノート

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