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Potassium Iodide → Ammonia

HRID 1433281
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HRID 1433281 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:44]=[CH:43][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:17]([C@@H:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=2)=[CH:8][CH:7]=1.[CH2:45]([O:52][C:53]1[CH:54]=[CH:55][C:56]([C@@H:64]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[CH2:65]Br)=[C:57]2[C:62]=1[NH:61][C:60](=[O:63])[CH:59]=[CH:58]2)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[I-].[K+].C(=O)([O-])O.[Na+].C(#N)CC>C(OCC)(=O)C.O>[NH3:3].[CH2:45]([O:52][C:53]1[CH:54]=[CH:55][C:56]([C@@H:64]([O:67][Si:68]([C:71]([CH3:72])([CH3:74])[CH3:73])([CH3:70])[CH3:69])[CH2:65][NH:3][CH2:4][CH2:5][C:6]2[CH:44]=[CH:43][C:9]([O:10][CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([O:35][CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[C:17]([C@@H:19]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=3)=[CH:8][CH:7]=2)=[C:57]2[C:62]=1[NH:61][C:60](=[O:63])[CH:59]=[CH:58]2)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1
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참가 물질

9

반응물 5

HCID 4875Potassium IodideHCID 7854PropionitrileHCID 516892Sodium BicarbonateHCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 86616485(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt

생성물 2

HCID 222
Ammonia
HCID 579332168-(benzyloxy)-5-[(1R)-2-({2-[4-(2-(4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]quinolin-2(1H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt (Preparation 42, 800 mg, 1.25 mmol), 8-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]quinolin-2(1H)-one (Prepared according to WO2005/092861, 615 mg, 1.25 mmol), potassium iodide (210 mg, 1.25 mmol), sodium hydrogen carbonate (630 mg, 7.5 mmol) were added to propionitrile (15 ml) and stirred at 100° C. under nitrogen overnight. The mixture was cooled and water (100 ml) and ethyl acetate (100 ml) added. Organics were separated and washed with water (100 ml) then brine (50 ml), dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 90/10/1 by volume) to furnish the title compound as a gum, 297 mg.

후처리

  1. temperatureThe mixture was cooled
  2. customOrganics were separated
  3. washwashed with water (100 ml)
  4. dry with materialbrine (50 ml), dried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-6386b8438267420e85e1deb139ee9ba3
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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