HCID 86711379, 화합물 → 9-Propyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 926293노트

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HRID 926293 반응식
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12.[Br-].[CH2:20]([Zn+])[CH2:21][CH3:22]>O1CCOCC1>[CH2:20]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12)[CH2:21][CH3:22]

참가 물질

4

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HCID 86711379HCID 86711379, 화합물HCID 178455869HCID 178455869, 화합물

생성물 1

HCID 899806809-Propyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

90-1. To a degassed solution of 9-iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (1.0 g, 2.82 mmol) and propylzinc(II)-bromide (14.1 mL, 7.05 mmol, 0.5M in THF) in dioxane (28 mL) was added PEPPSI-iPr (0.29 g, 0.424 mmol) under argon and the mixture was heated in a pressure vessel at 120° C. for 2.5 h. The reaction mixture was allowed to warm to rt and the solvent was removed under reduced pressure. The residue was suspended in DCM/MeOH (9:1, v/v), filtrated through a pad of celite and the filtrate was evaporated under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: from 1% MeOH in DCM to 10% MeOH in DCM in 35 min) to yield the product as an oil. The title compound was crystallized from diethyl ether to afford yellow crystals (370 mg). UPLC-MS: MS 271.2 (M+H+); UPLC rt 0.86 min.

후처리

  1. temperatureto warm to rt
  2. customthe solvent was removed under reduced pressure
  3. filtrationv/v), filtrated through a pad of celite
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: from 1% MeOH in DCM to 10% MeOH in DCM in 35 min)

출처 및 근거

ORD 기록
ord-fcfe984a7f034b21b99a57463aa20f44
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284331B2

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