[(1s,4s)-4-Aminocyclohexyl]methanol hydrochloride → (4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanol

HRID 1947042

반응식

HRID 1947042 반응식
CS([C:4]1[N:9]=[C:8]([N:10]2[C:18]3[C:13](=[C:14]([O:19][CH2:20][CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)[CH:7]=[CH:6][N:5]=1)=O.Cl.[NH2:28][CH:29]1[CH2:34][CH2:33][CH:32]([CH2:35][OH:36])[CH2:31][CH2:30]1>CCO>[CH3:26][S:23]([CH2:22][CH2:21][CH2:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[CH:11][N:10]2[C:8]1[CH:7]=[CH:6][N:5]=[C:4]([NH:28][CH:29]2[CH2:34][CH2:33][CH:32]([CH2:35][OH:36])[CH2:31][CH2:30]2)[N:9]=1)(=[O:25])=[O:24]

참가 물질

4

반응물 2

HCID 24194144[(1s,4s)-4-Aminocyclohexyl]methanol hydrochlorideHCID 580170861-(2-methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole

생성물 1

HCID 59743554(4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanol수율 49.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1-(2-Methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (5.0 g, 13 mmol) and (4-amino-cyclohexyl)-methanol hydrochloride (2.46 g, 19 mmol) were heated at reflux in EtOH (100 mL) under N2 for 16 h. The reaction mixture was then cooled, the suspension filtered, the filtrate volume reduced by half, diluted with EtOAc and washed with water, dried over sodium sulfate, filtered and concentrated until precipitate formed. This suspension was filtered, and the filtrate concentrated again until precipitation, and the suspension filtered, and both precipitates were combined and solvent removed in vacuo to yield (4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanol (Compound 214, 2.93 g), as a light yellow powder.

후처리

  1. temperatureThe reaction mixture was then cooled
  2. filtrationthe suspension filtered
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated until precipitate
  8. customformed
  9. filtrationThis suspension was filtered
  10. concentrationthe filtrate concentrated again until precipitation
  11. filtrationthe suspension filtered
  12. customsolvent removed in vacuo

출처 및 근거

ORD 기록
ord-19a75e557df24e2e9700fd95e96e12f1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399462B2

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