Cesium carbonate → 2-{3-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-isoindole-1,3-dione

HRID 8250

反応式

HRID 8250 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.Br[CH2:27][CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:27][CH2:28][CH2:29][N:30]4[C:34](=[O:35])[C:33]5[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:31]4=[O:40])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 21611N-3-BromopropylphthalimideHCID 1355066154-(2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-ol

生成物 1

HCID 103013902-{3-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-isoindole-1,3-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (0.100 g, 0.305 mmol), N-(3-bromopropyl)-phthalimide (0.163 g, 0.609 mmol, 2.0 equiv) and cesium carbonate (0.248 g, 0.761 mmol, 2.50 equiv) are combined in N,N-dimethylformamide (1.0 mL) and the reaction is heated at 60° C. for 48 hours. The reaction is diluted with water (1 mL) and the reaction mixture is partitioned between ethyl acetate (6 mL) and water (5 mL). The organic layer is removed and placed on a 10 g SCX resin column. The resin is washed sequentially with dichloromethane (20 mL) and 4:1 dichloromethane/2 N ammonia in methanol (125 mL). The latter fractions are evaporated to dryness and the residue is subjected to chromatography on silica gel (20 g) (9:1 ethyl acetate: methanol (2 N ammonia)) to yield the desired product as a tan solid, 0.117 g (75%).

後処理

  1. customthe reaction mixture is partitioned between ethyl acetate (6 mL) and water (5 mL)
  2. customThe organic layer is removed
  3. washThe resin is washed sequentially with dichloromethane (20 mL) and 4:1 dichloromethane/2 N ammonia in methanol (125 mL)
  4. customThe latter fractions are evaporated to dryness

出典と根拠

ORDレコード
ord-a2755ef9035543b8ab8943dbf0a2beed
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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