N,N'-Dimethylethylenediamine → Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate

HRID 57870

반응식

HRID 57870 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.Br[C:12]1[N:17]=[C:16]([N:18]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19]2)[CH:15]=[N:14][CH:13]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:12]3[N:17]=[C:16]([N:18]4[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19]4)[CH:15]=[N:14][CH:13]=3)[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridineHCID 86707065Tert-butyl 4-(6-bromopyrazin-2-yl)-1,4-diazepane-1-carboxylate

생성물 1

HCID 86707066Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate수율 25.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (2.0 mmol; 307 mg), tert-butyl 4-(6-bromopyrazin-2-yl)-1,4-diazepane-1-carboxylate (2.199 mmol; 785.5 mg), N,N′-Dimethylethylenediamine (4.0 mmol; 352.4 mg; 0.398 mL), cuprous iodide (2.0 mmol; 380.72 mg), and potassium carbonate (2.1990 mmol; 307 mg) in 1,4-Dioxane (15 mL) was purged with Argon, then sealed and stirred at 110° C. overnight. The mixture was cooled to room temperature, then filtered through Celite. The filtrate was concentrated; the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate as an off-white solid (217.2 mg, 25%). MS (ESI) m/z: δ 430 [M+H]+

후처리

  1. customwas purged with Argon
  2. customsealed
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified on silica
  7. washeluted with 0 to 100% EtOAc in Heptane

출처 및 근거

ORD 기록
ord-70c68bcf541c473dbdd1b6a191abd611
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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