Triethylamine → HCID 21949267, 화합물

HRID 2215591노트

반응식

HRID 2215591 반응식
[CH:1]([NH:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)=[O:6])([CH3:3])[CH3:2].[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27]C)[CH3:25].ClC(OC1C=CC=CC=1)=[O:33].N1CCCC1>O1CCCC1.CN(C)C=O.O>[CH:1]([NH:4][C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:27]([N:26]4[CH2:29][CH2:30][CH2:25][CH2:24]4)=[O:33])[CH:18]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)=[O:6])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 21949335HCID 21949335, 화합물

생성물 1

HCID 21949267HCID 21949267, 화합물수율 55%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

N1-Isopropyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide (90 mg, 0.29 mmol) was suspended in tetrahydrofuran (2 ml) at room temperature; triethylamine (0.121 mg, 0.868 mmol) and phenyl chloroformate (0.08 ml, 0.633 mmol) was added thereto while stirring; and the reaction mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture; this was subjected to extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. N,N-Dimethylformamide (1 ml) and pyrrolidine (0.2 ml, 2.39 mmol) was added to the residue, and stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure; and the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol). The resultant was washed with a solvent mixture (ether:hexane=1:1); and the solid was filtered off to yield the title compound as crystals (65 mg).

후처리

  1. stirringand the reaction mixture was stirred at room temperature for 2 hours
  2. extractionthis was subjected to extraction with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringstirred at room temperature overnight
  7. customThe reaction mixture was partitioned between ethyl acetate and water
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. concentrationThis solution was concentrated under reduced pressure
  10. customand the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol)
  11. washThe resultant was washed with a solvent mixture (ether:hexane=1:1)
  12. filtrationand the solid was filtered off

출처 및 근거

ORD 기록
ord-c9811bebe4c24d4fa317973e1c873dc0
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109219B2

반응 노트

불러오는 중…