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Potassium Carbonate → N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

HRID 870211
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HRID 870211 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[C:13]([Cl:19])[CH:14]=[C:15]([Cl:18])[CH:16]=3)[CH2:11][N:10]([CH3:20])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[N:21]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][NH2:35])=[N+:22]=[N-:23].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[N:21]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][NH:35][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[C:17]3[C:12](=[C:13]([Cl:19])[CH:14]=[C:15]([Cl:18])[CH:16]=3)[CH2:11][N:10]([CH3:20])[CH2:9]2)[CH:3]=1)=[N+:22]=[N-:23]
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 27352801-Amino-11-azido-3,6,9-trioxaundecaneHCID 223869034-(3-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline2회

생성물 1

HCID 86699380N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

시약·촉매·용매

2
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
90 °C

실험 절차

Into a 10-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-(3-bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline (intermediate 1.4) (400 mg, 1.08 mmol, 1.00 equiv) in DMSO (6 mL), 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine (236.11 mg, 1.08 mmol, 1.00 equiv), (S)-pyrrolidine-2-carboxylic acid (24.79 mg, 0.21 mmol, 0.20 equiv), copper(I) iodide (20.48 mg, 0.11 mmol, 0.10 equiv) and potassium carbonate (223.18 mg, 1.62 mmol, 1.50 equiv). The resulting solution was stirred at 90° C. in an oil bath and the reaction progress was monitored by LCMS. After stirring overnight the reaction mixture was cooled with a water/ice bath and then diluted with ice water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic extracts were combined and washed with 2×20 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1). This resulted in 130 mg (24%) of N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenamine as yellow oil.

후처리

  1. customInto a 10-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringAfter stirring overnight the reaction mixture
  4. temperaturewas cooled with a water/ice bath
  5. extractionThe resulting solution was extracted with 3×30 mL of ethyl acetate
  6. washwashed with 2×20 mL of brine
  7. dry with materialThe mixture was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 130 mg (24%) of N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenamine as yellow oil

출처 및 근거

ORD 기록
ord-83ca9d6508644bf1adb925e5c5b6e46a
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969377B2

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