1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-Methoxy-3-(4-nitro-pyrazol-1-yl)-1-oxa-9-aza-phenanthren-2-one

HRID 2273194Notes

Reaction equation

C(=O)([O-])O.[Na+].[N+:6]([C:9]1[CH:10]=[N:11][N:12]([CH2:14][C:15]([OH:17])=[O:16])[CH:13]=1)([O-:8])=[O:7].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.O[C:43]1[CH:44]=[N:45][C:46]2[C:51]([C:52]=1[CH:53]=O)=[CH:50][C:49]([O:55][CH3:56])=[CH:48][CH:47]=2.N12CCCN=C1CCCCC2>CN(C)C=O.O>[CH3:56][O:55][C:49]1[CH:50]=[C:51]2[C:46](=[CH:47][CH:48]=1)[N:45]=[CH:44][C:43]1[O:16][C:15](=[O:17])[C:14]([N:12]3[CH:13]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=[N:11]3)=[CH:53][C:52]2=1

Participants

Procedure

Sodium hydrogen carbonate (4.96 g, 59.06 mmol, 3.0 eq) is added at room temperature to a stirred solution of (4-nitro-pyrazol-1-yl)-acetic acid (3.77 g, 21.65 mmol, 1.1 eq) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (14.97 g, 39.37 mmol, 2.0 eq) in N,N-dimethylformamide (200 mL). After 1 h 30 stirring at room temperature 3-hydroxy-6-methoxy-quinoline-4-carbaldehyde (4.0 g, 19.69 mmol, 1.0 eq) is added and the resulting mixture is stirred at room temperature for 3 hours before the addition of 1,8-diazabicyclo[5,4,0]undec-7-ene (11.8 mL, 78.74 mmol, 4.0 eq). After 48 hours stirring at room temperature, the reaction mixture is poured into water (1000 mL) and the resulting solid is collected by filtration to afford 6-methoxy-3-(4-nitro-pyrazol-1-yl)-1-oxa-9-aza-phenanthren-2-one as a yellow solid (4.0 g, 57% yield).

Workup

filtrationthe resulting solid is collected by filtration

Sources & evidence

ORD record: ord-08a9cfbac522433eb63cd9b2bd2539e7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120822B2

Reaction notes

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Reaction equation

Participants

Reactant 5

Product 1

Reagents, catalysts & solvents 2

Procedure

Workup

Sources & evidence

Reaction notes