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

HRID 1947042ノート

反応式

HRID 1947042 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-19a75e557df24e2e9700fd95e96e12f1
出典データセット
uspto-grants-2013_03
特許番号
US08399462B2

反応ノート

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