m-Chloroperbenzoic acid → 1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-5-oxido-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine

HRID 606082Notes

Reaction equation

HRID 606082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][N:14]3[C:26]4[C:25]5[N:24]=[CH:23][CH:22]=[CH:21][C:20]=5[N:19]=[CH:18][C:17]=4[N:16]=[C:15]3[CH2:27][CH2:28][CH3:29])[O:10][N:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:38])C=1>C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][N:14]3[C:26]4[C:25]5[N:24]=[CH:23][CH:22]=[CH:21][C:20]=5[N+:19]([O-:38])=[CH:18][C:17]=4[N:16]=[C:15]3[CH2:27][CH2:28][CH3:29])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 670413321-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine

Product 1

HCID 670414151-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-5-oxido-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The method described in Part E of Example 12 was used to treat 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine (1.08 g, 2.79 mmol) with mCPBA (1.1 g of 75% pure material followed by 0.35 g) with the modification that the trituration of the crude product was carried out with diethyl ether. 1-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-5-oxido-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridine was obtained as a white solid.

Sources & evidence

ORD record
ord-47c45b5c6b114580accb1bd152280893
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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