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

HRID 606080Notes

Reaction equation

HRID 606080 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[CH3:27])[O:10][N:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>>[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-:36])=[CH:18][C:17]=4[N:16]=[C:15]3[CH3:27])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 670412981-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c][1,5]naphthyridine

Product 1

HCID 670413221-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridine

Procedure

The method described in Part E of Example 12 was used to treat 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c][1,5]naphthyridine (1.15 g, 3.20 mmol) with mCPBA (0.94 g of 75% pure material followed by 0.25 g) to provide 1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridine as a dark yellow solid.

Sources & evidence

ORD record
ord-91b24b8d43a04985a0d2a255243fa74a
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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