Dimethylformamide → HCID 59351757, compound

HRID 1889402Notes

Reaction equation

[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=O)[O:9]C(=O)[C:5]=2[CH:4]=1)[CH3:2].[N-:29]=[N+]=[N-].[Na+].CN(C)C=O>C(OCC)(=O)C>[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=[O:9])[NH:29][C:5]=2[CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4′-[(6-ethyl-2,4-dioxo-2H-thieno[2,3-d][1,3]oxazine-1(4H)-yl)methyl]biphenyl-2-carbonitrile (3.5 g), sodium azide (0.88 g) and N,N-dimethylformamide (50 mL) was stirred at 50° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in toluene (30 mL), and the mixture was stirred at 110° C. for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (1.5 g, 46%).

Workup

washwashed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
dissolutionThe obtained residue was dissolved in toluene (30 mL)
stirringthe mixture was stirred at 110° C. for 20 hr
concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c2bc01fa6d8f441ab9aca10a17f83357
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501750B2

Reaction notes

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