Tetrahydrofuran → 1-(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)ethanone
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](N(OC)C)=[O:23])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:28]=2)=[N:7][C:6]([CH3:29])=[N:5]1)([CH3:3])[CH3:2].O1CCC[CH2:31]1.C[Mg]Br>CCOCC>[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](=[O:23])[CH3:31])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:28]=2)=[N:7][C:6]([CH3:29])=[N:5]1)([CH3:3])[CH3:2]참가 물질
반응물 3
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 0 °C
실험 절차
2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-N-methoxy-N-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide (2.0 g, 0.0050 mol) was dissolved in Tetrahydrofuran (20 mL, 0.3 mol). The reaction was cooled at 0° C. 3.0 M of Methylmagnesium bromide in Ether was added dropwise. The reaction was allowed to warm to room temperature over a 1 hour period. LCMS shows complete conversion to desired product. The reaction was cooled back to 0° C. and quenched with saturated aqueous ammonium chloride. The reaction mixture was diluted with H2O and the crude product was extracted with Ethyl Acetate The organic extracts were combined, dried over Na2SO4, filtered and concentrated to dryness. The crude was purified on silica gel (0→10% MeOH/DCM) to yield 1-(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)ethanone as an orange solid.
후처리
- temperatureto warm to room temperature over a 1 hour period
출처 및 근거
- ORD 기록
- ord-fec465046586424093e3b5c3bf1f58b1
- 출처 데이터셋
- uspto-grants-2015_07
- 특허 번호
- US09090628B2
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