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Acetic Acid → HCID 86682449, 화합물

HRID 715874
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HRID 715874 반응식
[F:1][C:2]1([F:47])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30](C=O)=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[CH2:4][CH2:3]1.[C:48]([OH:51])(=O)[CH3:49].[CH3:52][NH:53][CH2:54]CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[F:1][C:2]1([F:47])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:52][N:53]([CH2:49][CH2:48][OH:51])[CH3:54])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:38][CH:37]=2)[CH2:6][CH2:7]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

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HCID 176Acetic AcidHCID 80162-(Methylamino)ethanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86682450HCID 86682450, 화합물

생성물 1

HCID 86682449HCID 86682449, 화합물수율 89%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 70 mg (0.11 mmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-formyl pyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol obtained in Example (36-1) in 1.0 ml of tetrahydrofuran, 6.1 μl (0.11 mmol) of acetic acid, 26 μl (0.32 mmol) of 2-(methylamino)ethanol and 68 mg (0.32 mmol) of sodium triacetoxyborohydride were added, and the reaction solution was stirred at room temperature for 3 hours. After completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was added to the reaction solution and the reaction solution was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [dichloromethane/methanol/28% ammonia aqueous solution=95/4.75/0.25-80/19/1 (V/V/V)] to provide 68 mg of the title compound as a white solid (yield: 89%).

후처리

  1. additionwas added to the reaction solution
  2. extractionthe reaction solution was extracted with dichloromethane
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-fbb991cb11e24532905683d86dfbd679
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187450B2

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