Toluene → Ethyl 1-((4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)-1H-pyrazole-4-carboxylate

HRID 928423Notes

Reaction equation

O[CH2:2][C:3]1[CH:14]=[CH:13][C:6]2[O:7][CH2:8][C:9](=[O:12])[N:10]([CH3:11])[C:5]=2[CH:4]=1.C([C:17]1[C:21]([C:22]([O-:24])=[O:23])=[CH:20][NH:19][N:18]=1)C.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:26]=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:11][N:10]1[C:9](=[O:12])[CH2:8][O:7][C:6]2[CH:13]=[CH:14][C:3]([CH2:2][N:18]3[CH:17]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]=[N:19]3)=[CH:4][C:5]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred, cooled (0° C.) solution of 6-(hydroxymethyl)-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (122 mg, 0.631 mmol), ethylpyrazol-4-carboxylate (88 mg, 0.631 mmol) and triphenylphosphine (248 mg, 0.947 mmol) in THF (5 ml) was added dropwise a 40% solution of DEAD in toluene (0.375 ml, 0.947 mmol). The reaction mixture was stirred for 2 h at 0° C., then over night at 20° C. Saturated aqueous NaHCO3 was added and the mixture was extracted with AcOEt. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound. MS (Method A) [M+H]+=316.9

Workup

waitover night at 20° C
extractionthe mixture was extracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-12722edfe09a4328a869ad8a9e83879a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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