Water → N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-(2-(6-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-4-yloxy)ethyl)benzenesulfonamide

HRID 2387955노트

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HRID 2387955 반응식
[H-].[Na+].[CH:3]1([N:6]([CH2:20][CH2:21][OH:22])[S:7]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH3:19])(=[O:9])=[O:8])[CH2:5][CH2:4]1.Cl[C:24]1[N:29]=[CH:28][N:27]=[C:26]([N:30]2[CH2:35][CH2:34][C:33]3([CH2:40][CH2:39][N:38]([C:41]4[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=4)[CH2:37][CH2:36]3)[CH2:32][CH2:31]2)[CH:25]=1.O>O1CCCC1.C(OCC)(=O)C>[CH:3]1([N:6]([CH2:20][CH2:21][O:22][C:24]2[CH:25]=[C:26]([N:30]3[CH2:31][CH2:32][C:33]4([CH2:36][CH2:37][N:38]([C:41]5[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=5)[CH2:39][CH2:40]4)[CH2:34][CH2:35]3)[N:27]=[CH:28][N:29]=2)[S:7]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH3:19])(=[O:9])=[O:8])[CH2:4][CH2:5]1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 43577600N-Cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamideHCID 59401695HCID 59401695, 화합물

생성물 1

HCID 46207142N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-(2-(6-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)pyrimidin-4-yloxy)ethyl)benzenesulfonamide수율 7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of sodium hydride (7.28 mmol, 10 equiv.) in tetrahydrofuran (10 ml) there was added, at 0° C., N-cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamide (C-10) (0.8 mmol, 1.1 equiv.), followed by 3-(6-chloro-pyrimidin-4-yl)-9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane (0.73 mmol, 1 equiv.). The reaction mixture was stirrred overnight at room temperature; water was then added and the mixture was diluted with ethyl acetate. The organic phase was extracted with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (Alox-neutral). Yield: 7%. Rt=3.4 min; m/z=607.5 [MH]+

후처리

  1. additionwas added, at 0° C.
  2. extractionThe organic phase was extracted with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (Alox-neutral)

출처 및 근거

ORD 기록
ord-fdc62f7b7c2544b5af25e2e6180443b7
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08269000B2

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