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

반응식

HRID 16435 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 77202-Ethylhexanol용매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30b698dcf3db4e6b9e7782296266353a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737153B2

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