Lithium hydroxide, monohydrate → N-{4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine

HRID 1159999노트

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HRID 1159999 반응식
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:37]=[C:36]5[C:31]([CH2:32][CH2:33][N:34]([CH3:38])[CH2:35]5)=[CH:30][CH:29]=4)[N:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:7]=1)=O.O[Li].O>O1CCCC1.O.C(Cl)Cl>[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:37]=[C:36]5[C:31]([CH2:32][CH2:33][N:34]([CH3:38])[CH2:35]5)=[CH:30][CH:29]=4)[N:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 595137262,2,2-Trifluoro-N-[3-(3-{2-[(2-methyl-1,2,3,4-tetrahydro-7-isoquinolinyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]acetamide

생성물 1

HCID 59511387N-{4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine수율 92%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution of 2,2,2-trifluoro-N-[3-(3-{2-[(2-methyl-1,2,3,4-tetrahydro-7-isoquinolinyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]acetamide (290 mg, 0.53 mmol) in tetrahydrofuran (2 mL) and deionized water (2 mL) was added LiOH.H2O (34 mg, 0.80 mmol). The reaction was heated to 50° C. for 3 h, and then diluted with 10 mL DCM. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over Na2SO4, filtered, and concentrated to generate the title compound in 92% yield (219 mg, 0.49 mmol). 1H NMR (400 MHz, d6-DMSO) δ 9.41 (s, 1H), 8.79 (d, J=6.8 Hz, 1H), 8.52 (bd, 1H), 8.21 (d, J=5.3 Hz, 1H), 7.53 (s, 1H), 7.41-7.46 (m, 2H), 7.08-7.15 (m, 2H), 7.00 (d, J=8.2 Hz, 1H), 6.80 (s, 1H), 6.67 (t, J=7.7 Hz, 1H), 6.49 (d, J=5.3 Hz, 1H), 5.25 (s, 2H), 3.42 (s, 2H), 2.76 (t, J=5.7 Hz, 2H), 2.58 (t, J=5.7 Hz, 2H), 2.32 (s, 3H). MS (ESI) m/z=448 [M+H]+.

후처리

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-81ba8cde4d2c4bec8281024ffe614919
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812022B2

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