Diisopropylethylamine → 2-(4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-propan-2-ol

HRID 1947043ノート

反応式

HRID 1947043 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.C([O-])(=O)C.[OH:31][C:32]([CH:35]1[CH2:40][CH2:39][CH:38]([NH3+:41])[CH2:37][CH2:36]1)([CH3:34])[CH3:33].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[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:41][CH:38]2[CH2:39][CH2:40][CH:35]([C:32]([OH:31])([CH3:33])[CH3:34])[CH2:36][CH2:37]2)[N:9]=1)(=[O:25])=[O:24]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 580170861-(2-methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indoleHCID 693071524-(2-Hydroxyprop-2-yl)-cyclohexylammonium acetate

生成物 1

HCID 597435712-(4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-propan-2-ol収率 59%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
126 °C

実験手順

1-(2-Methanesulfinyl-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (538 mg, 1.4 mmol), 4-(2-hydroxyprop-2-yl)-cyclohexylammonium acetate (400 mg, 2 mmol), and DIEA (0.8 mL, 5 mmol) were combined in NMP (10 mL) and heated to 126° C. in a sealed tube for 4 h, cooled, and partitioned between water and EtOAc. The organic layer was separated and washed twice with water, dried over sodium sulfate, filtered and purified by flash chromatography (SiO2) with 3:97 MeOH/DCM, and recrystallized from MeOH/DCM, triturated with EtOAc and solvent evaporated to yield 2-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-propan-2-ol (Compound 166, 391 mg, 59%) as a white powder.

後処理

  1. temperaturecooled
  2. custompartitioned between water and EtOAc
  3. customThe organic layer was separated
  4. washwashed twice with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by flash chromatography (SiO2) with 3:97 MeOH/DCM
  8. customrecrystallized from MeOH/DCM
  9. customtriturated with EtOAc and solvent
  10. customevaporated

出典と根拠

ORDレコード
ord-064ebfc4d3f0476bb4c2591b507c469e
出典データセット
uspto-grants-2013_03
特許番号
US08399462B2

反応ノート

読み込み中…