Methoxyisopropylamine → HCID 69482655, compound

HRID 2364239Notes

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:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:26][CH:27]([NH2:31])[CH2:28][O:29][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:25])=[C:14]([C:20]([NH:31][CH:27]([CH3:26])[CH2:28][O:29][CH3:30])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 123458Methoxyisopropylamine

HCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482655HCID 69482655, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyisopropylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.80 (1H, br s), 10.80 (1H, br s), 10.05 (1H, br s), 8.18 (0.45H, s), 8.14(0.55H, s), 7.35-7.24 (3H, m), 7.15-7.08 (2H, m), 4.15-4.07 (1H, m), 3.98 (2H, s), 3.40-3.35 (5H, m), 1.15 (0.45H, d, J=6.6 Hz), 1.09 (0.55H, d, J=6.6 Hz); HRMS calcd for C20H20FN3O4+H+: 386.1516. Found 386.1513.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-56f8634700fe4b36962ccfe4e24a2f2d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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