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

HRID 1530670Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperatureto warm to room temperature over a 1 hour period

Sources & evidence

ORD record: ord-fec465046586424093e3b5c3bf1f58b1
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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