(Dimethyl sulfide)trihydroboron → N-(4-methoxybenzyl)-2-methyl-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528574Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]([C:24]2[S:25][CH:26]=[CH:27][N:28]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][C:19](=O)[CH:18]([CH3:22])[O:17][C:16]=3[CH:23]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CSC.B>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C:24]2[S:25][CH:26]=[CH:27][N:28]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH:18]([CH3:22])[O:17][C:16]=3[CH:23]=2)(=[O:11])=[O:10])=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of N-(4-methoxybenzyl)-2-methyl-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (1.45 g, 3.14 mmol) in THF (25 ml.) was added borane dimethyl sulfide (1M in THF) (0.343 g, 4.71 mmol, Aldrich) at 0° C. and reaction mixture was stirred at 25° C. for 5 h. The reaction mixture was quenched with MeOH (15 mL) and the solvent was removed under vacuum. The residue obtained was diluted with MeOH and stirred at 25° C. for 1 h, then concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using a gradient of 0-50% EtOAc in hexanes as the eluent to afford 1.3 g of N-(4-methoxybenzyl)-2-methyl-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (INTERMEDIATE AE) as off white solid in 92% yield.

Workup

customreaction mixture
customThe reaction mixture was quenched with MeOH (15 mL)
customthe solvent was removed under vacuum
customThe residue obtained
stirringstirred at 25° C. for 1 h
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-284c58952a284629bd9e61657c787a6f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346798B2

Reaction notes

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