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Hydrochloric Acid → 2-[2-({3-[4-(2-oxopyrrolidin-1-yl)phenoxy]propyl}pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

HRID 1504183
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HRID 1504183 반응식
Br[C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12][N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:4][CH:3]=1.[NH:33]1[CH2:37][CH2:36][CH2:35][C:34]1=[O:38].C(=O)([O-])[O-].[K+].[K+].CNCCNC.[ClH:51]>[Cu](I)I.C(O)C.C1(C)C=CC=CC=1>[ClH:51].[ClH:51].[O:38]=[C:34]1[CH2:35][CH2:36][CH2:37][N:33]1[C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12][N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:4][CH:3]=1
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참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 669599672-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one

생성물 1

HCID 66960533
2-[2-({3-[4-(2-oxopyrrolidin-1-yl)phenoxy]propyl}pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 702Ethanol용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

2-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one(500 mg), 2-pyrrolidone(0.228 ml), potassium carbonate(415 mg), copper iodide (I) (190 mg), and N,N′-dimethyl ethylenediamine(0.39 ml) were added to toluene(5 ml). The mixture was stirred at 100° C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature. After adding aqueous ammonia, extraction was performed using ethyl acetate. The organic layer was washed with saturated saline, and dried with sodium sulfate. After the organic layer was condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate: methanol=100:0→70:30). The purified product was condensed under reduced pressure. A condensed hydrochloric acid(0.3 ml) was added to an ethanol solution of the residue, followed by condensation under reduced pressure. The residue was recrystallized from isopropyl alcohol/water to give the title compound(350 mg) as a white powder.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionAfter adding aqueous
  3. extractionammonia, extraction
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried with sodium sulfate
  6. customcondensed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=100:0→70:30)
  8. customcondensed under reduced pressure
  9. customfollowed by condensation under reduced pressure
  10. customThe residue was recrystallized from isopropyl alcohol/water

출처 및 근거

ORD 기록
ord-87861d46f2ba46a181731dd1b1790dbc
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09212187B2

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