Methanesulfonyl chloride → 5-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxymethyl]-pyrrolidin-2-one

HRID 8251

反応式

HRID 8251 の反応式
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.CS(Cl)(=O)=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[C:21]([C:28]2[C:37]3[C:32](=[CH:33][C:34](O)=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[C:22]2[CH2:27][CH2:26][CH2:25][N:23]2[N:24]=1>CN(C)C=O>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[C:21]([C:28]2[C:37]3[C:32](=[CH:33][C:34]([O:1][CH2:2][CH:3]4[NH:7][C:6](=[O:8])[CH2:5][CH2:4]4)=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[C:22]2[CH2:27][CH2:26][CH2:25][N:23]2[N:24]=1

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinoneHCID 1355066154-(2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-ol

生成物 1

HCID 102242605-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxymethyl]-pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of (R)-(−)-5-(hydroxymethyl)-2-pyrrolidinone (315 mg, 2.74 mmol) in N,N-dimethylformamide (3 mL) is treated with methansulfonyl chloride (320 mg, 2.74 mmol) and heated at 60° C. for 5 h. The reaction mixture is diluted with N,N-dimethylformamide (1 mL) and 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (200 mg, 0.91 mmol) added. The mixture is stirred at 60° C. for additional 16 h, cooled to room temperature, and partitioned between ethyl acetate and water. The organic portion is washed three times with water, once with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The crude residue is chromatographed on SiO2 (89% dichloromethane 10% methanol 1% concentrated ammonium hydroxide) to yield the title compound, 32 mg (8%), as a light red solid.

後処理

  1. additionadded
  2. temperaturecooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. washThe organic portion is washed three times with water
  5. dry with materialonce with brine, dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue is chromatographed on SiO2 (89% dichloromethane 10% methanol 1% concentrated ammonium hydroxide)

出典と根拠

ORDレコード
ord-ba620833bb654b8b8301ec37ef3e1997
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

関連ノート

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