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 1530675ノート

反応式

HRID 1530675 の反応式
[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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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

出典と根拠

ORDレコード
ord-5c44210e2fd842b9869f6547478259d7
出典データセット
uspto-grants-2015_07
特許番号
US09090628B2

反応ノート

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