Phosphorus oxide (P4O10) → HCID 178462937, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[N:7]([CH2:12][CH3:13])[C:6](=[O:14])[C:5]2([CH3:16])[CH3:15].[N+:17]([C:20]1[C:21]([C:25](O)=O)=[N:22][NH:23][CH:24]=1)([O-:19])=[O:18].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH2:12]([N:7]1[C:8]2[CH:9]=[C:10]3[N:11]=[C:25]([C:21]4[C:20]([N+:17]([O-:19])=[O:18])=[CH:24][NH:23][N:22]=4)[NH:1][C:2]3=[CH:3][C:4]=2[C:5]([CH3:15])([CH3:16])[C:6]1=[O:14])[CH3:13]Participants
Conditions
- Temperature
- 150 °C
Procedure
5,6-Diamino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one (5.00 g, 22.80 mmol), and 4-nitro-pyrazole carboxylic acid (3.58 g, 22.80 mmol) were mixed with polyphosphoric acid (22.34 g, 228.0 mmol) and phosphorus pentoxide (1.63 g, 11.4 mmol) and stirred under nitrogen at 150° C. for 6 h. It was quenched with ice water (250 ml) and the resulting suspension was adjusted to pH 5 by adding aqueous ammonia. The crude microcrystalline solid was dissolved in ethyl acetate (400 mL). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (4×400 mL). After evaporation of the solvent, the crude product was purified by HPLC (High Performance Liquid Chromatography). 5-Ethyl-7,7-dimethyl-2-(4-nitro-1H-pyrazol-3-yl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one was obtained as an orange solid (2.47 g, 32%).
Workup
- customIt was quenched with ice water (250 ml)
- additionby adding aqueous ammonia
- dissolutionThe crude microcrystalline solid was dissolved in ethyl acetate (400 mL)
- customThe organic layer was separated
- extractionthe aqueous layer was further extracted with ethyl acetate (4×400 mL)
- customAfter evaporation of the solvent
- customthe crude product was purified by HPLC (High Performance Liquid Chromatography)
Sources & evidence
- ORD record
- ord-d86af2fd3dd542d0b05344901398af61
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462639B2
Reaction notes
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