Aluminium lithium hydride → 2-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropan-1-ol

HRID 1530675노트

반응식

HRID 1530675 반응식
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]5[N:26]([CH:27]6[CH2:32][CH2:31][CH2:30][N:29]([C:33]([CH3:40])([CH3:39])[C:34](OCC)=[O:35])[CH2:28]6)[N:25]=[CH:24][CH:23]=5)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:41]=2)=[N:7][C:6]([CH3:42])=[N:5]1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]5[N:26]([CH:27]6[CH2:32][CH2:31][CH2:30][N:29]([C:33]([CH3:40])([CH3:39])[CH2:34][OH:35])[CH2:28]6)[N:25]=[CH:24][CH:23]=5)=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:41]=2)=[N:7][C:6]([CH3:42])=[N:5]1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 68312882ethyl 2-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropanoate

생성물 1

HCID 683132872-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of ethyl 2-(3-(5-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropanoate (150 mg, 0.26 mmol) in Tetrahydrofuran (2.00 mL) at 0° C. was added Lithium Aluminum Hydride (1 mol/L) in THF (0.52 mL, 0.5238 mmol) dropwise. The reaction mixture was slowly allowed to warm up to room temperature and was stirred for 2 hours. LC-MS analysis of the reaction mixture showed no more starting material and the formation of the desired product. The reaction mixture was quenched by the addition of MeOH, filtered and the concentrated. The resulting oil was purified by rHPLC to give 266. 1H NMR (400 MHz, DMSO) δ 8.51 (d, J=8.3 Hz, 1H), 7.98-7.86 (m, 1H), 7.52 (d, J=1.5 Hz, 1H), 7.22 (dd, J=8.3, 1.4 Hz, 1H), 7.09 (s, 1H), 6.39 (t, J=6.8 Hz, 1H), 5.83 (dt, J=13.2, 6.6 Hz, 1H), 4.54 (d, J=15.0 Hz, 4H), 4.36-4.15 (m, 2H), 3.24 (d, J=4.9 Hz, 2H), 3.08 (d, J=8.5 Hz, 1H), 2.93 (t, J=15.9 Hz, 1H), 2.62-2.52 (m, 2H), 2.26 (s, 3H), 2.11 (t, J=10.8 Hz, 1H), 1.92 (s, 2H), 1.73 (d, J=13.1 Hz, 1H), 1.57-1.42 (m, 6H), 0.91 (s, 6H). LCMS: 531.3

출처 및 근거

ORD 기록
ord-5c44210e2fd842b9869f6547478259d7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090628B2

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