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 1422905노트

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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

참가 물질

실험 절차

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).

후처리

filtrationthe resulting solid is collected by filtration

출처 및 근거

ORD 기록: ord-00af50a335934d59af85abe14f14a964
출처 데이터셋: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08927541B2

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참가 물질

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생성물 1

시약·촉매·용매 2

실험 절차

후처리

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