Diisopropylethylamine → 4-[(4aR,7aR)-Octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-6-({4-[(3-amino-1,2-benz-isoxazol-4-yl)oxy]-3-fluorophenyl}amino)-2-pyrimidinylamine

HRID 16435

反応式

HRID 16435 の反応式
[NH2:1][C:2]1[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]4[CH:24]=[C:23](Cl)[N:22]=[C:21]([NH2:26])[N:20]=4)=[CH:14][C:13]=3[F:27])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]2[CH2:34][NH:35][CH2:36][C@H:29]12.C(N(C(C)C)CC)(C)C>C(C(CCCC)CO)C>[NH:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]2[CH2:34][N:35]([C:23]3[CH:24]=[C:19]([NH:18][C:15]4[CH:16]=[CH:17][C:12]([O:11][C:7]5[C:6]6[C:2]([NH2:1])=[N:3][O:4][C:5]=6[CH:10]=[CH:9][CH:8]=5)=[C:13]([F:27])[CH:14]=4)[N:20]=[C:21]([NH2:26])[N:22]=3)[CH2:36][C@H:29]12

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 1515156(4aR,7aR)-Octahydro-1H-pyrrolo(3,4-b)pyridineHCID 17979320N-{4-[(3-Amino-1,2-benzisoxazol-4-yl)oxy]-3-fluorophenyl}-N-(2-amino-6-chloro-4-pyrimidinyl)amine

生成物 1

HCID 684269204-[(4aR,7aR)-Octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-6-({4-[(3-amino-1,2-benz-isoxazol-4-yl)oxy]-3-fluorophenyl}amino)-2-pyrimidinylamine

試薬・触媒・溶媒 1

HCID 77202-Ethylhexanol溶媒

反応条件

温度
150 °C

実験手順

88 mg (0.23 mmol) of N-{4-[(3-amino-1,2-benzisoxazol-4-yl)oxy]-3-fluorophenyl}-N-(2-amino-6-chloro-4-pyrimidinyl)amine (from example 3) and 114.8 mg (0.91 mmol) of [(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridine together with 294.1 mg (2.28 mmol) of diisopropylethylamine are dissolved in 4 ml of 2-ethylhexanol, and the mixture is stirred at 150° C. for 3 h. After cooling, the reaction mixture is filtered and water is added. The mixture is extracted repeatedly with ethyl acetate, the organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

後処理

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. additionwater is added
  4. extractionThe mixture is extracted repeatedly with ethyl acetate
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by preparative HPLC

出典と根拠

ORDレコード
ord-30b698dcf3db4e6b9e7782296266353a
出典データセット
uspto-grants-2010_06
特許番号
US07737153B2

関連ノート

読み込み中…