2-Methoxyethylamine → HCID 69482190, compound

HRID 2364265Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([OH:26])=[C:15]([C:21](OCC)=[O:22])[C:16](=[O:20])[NH:17]2)=[N:12][CH:11]=1.[CH3:27][O:28][CH2:29][CH2:30][NH2:31]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([OH:26])=[C:15]([C:21]([NH:31][CH2:30][CH2:29][O:28][CH3:27])=[O:22])[C:16](=[O:20])[NH:17]2)=[N:12][CH:11]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 69480228HCID 69480228, compound

Product 1

HCID 69482190HCID 69482190, compound

Procedure

This compound was prepared from ethyl 7-[(2,4-difluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) tautomers are observed δ 11.70 (1H, br s), 10.79 (1H, br s), 10.19 (1H, br s), 8.18 (0.45H, s), 8.13 (0.55H, s), 7.43-7.36 (1H, m), 7.29-7.21 (2H, m) 7.08-7.05 (1H, m), 4.02 (2H, s), 3.44-3.37 (2H, m), 3.31 (3H, s), 3.26-3.20 (2H, m); HRMS calcd for C19H17F2N3O4+H+: 390.1265. Found 390.1255.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-38e29825e2b845459dcf3a49d52ac4f2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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