4-Nitrobenzaldehyde → Methyl 2-p-nitrophenyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-formate

HRID 63787Notes

Reaction equation

HRID 63787 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:12][N:13]1[C:17]([C:18](=[O:20])[NH2:19])=[CH:16][C:15]([C:21]([O:23][CH3:24])=[O:22])=[CH:14]1>>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]2[NH:19][C:18](=[O:20])[C:17]3=[CH:16][C:15]([C:21]([O:23][CH3:24])=[O:22])=[CH:14][N:13]3[N:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 66985220Methyl 1-amino-5-carbamoyl-1H-pyrrole-3-carboxylate

Product 1

HCID 136843825Methyl 2-p-nitrophenyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-formateYield 72%

Procedure

According to the general preparation method described in example 5 above, p-nitrobenzaldehyde reacts with compound 3 to give compound Ma as light yellow solid in 72.0% yield. m.p.>300° C. 1H NMR (300 MHz, DMSO-d6): δ 12.52 (s, 1H), 8.38 (d, J=8.5 Hz, 2H), 8.22 (s, 1H), 8.21 (d, J=8.5 Hz, 2H), 7.26 (s, 1H), 3.80 (s, 3H). LRMS (EI) m/z (%): 314 (M+, 85), 283 (100). HRMS calcd. C14H10N4O5: 314.0651. found: 314.0659.

Workup

  1. customAccording to the general preparation method
  2. customto give compound Ma as light yellow solid in 72.0% yield

Sources & evidence

ORD record
ord-7244964fa05d4bb09bff1097c61c2a67
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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