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 1422905Notes

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 h30 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-00af50a335934d59af85abe14f14a964
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927541B2

Reaction notes

Loading…

Reaction equation

Participants

Reactant 5

Product 1

Reagents, catalysts & solvents 2

Procedure

Workup

Sources & evidence

Reaction notes