O-Methylhydroxylamine → HCID 86612799, compound

HRID 2364522Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:28])=[C:14]([C:24]([NH:26][CH3:27])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][C:20]([OH:22])=O)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[O:29]([NH2:31])[CH3:30]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:28])=[C:14]([C:24]([NH:26][CH3:27])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][C:20]([NH:31][O:29][CH3:30])=[O:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 4113O-Methylhydroxylamine

HCID 69482851HCID 69482851, compound

Product 1

HCID 86612799HCID 86612799, compound

Procedure

This compound was prepared from [7-[(4-fluorophenyl)methyl]-4-hydroxy-3-[(methylamino)carbonyl]-2-oxo-1,5-naphthyridine-1(2H)-yl]acetic acid and methoxylamine employing methods similar to those described in example 558. The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.39 (1H, br s), 9.96 (1H, br s), 8.55 (1H, s), 7.88 (1H, s), 7.36-7.31 (2H, m), 7.14-7.09 (2H, m), 4.80 (2H, s), 4.11 (2H, s), 3.52 (3H, s), 2.88 (3H, d, J=4.8 Hz); HRMS calcd for C20H19FN4O5+H+: 415.1412. Found 415.1416.

Workup

customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-8811554fb38b4f95a9f08a4d2f2075c5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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