2-Methoxyethylamine → HCID 69482463, compound

HRID 2364554Notes

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:32])=[C:14]([C:28](OC)=[O:29])[C:15](=[O:27])[N:16]3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:33][O:34][CH2:35][CH2:36][NH2:37]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:32])=[C:14]([C:28]([NH:37][CH2:36][CH2:35][O:34][CH3:33])=[O:29])[C:15](=[O:27])[N:16]3[C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 69480433HCID 69480433, compound

Product 1

HCID 69482463HCID 69482463, compoundYield 89%

Procedure

In a similar manner to that described in example 196, from methyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (50 mg, 0.115 mmol) and [2-(methyloxy)ethyl]amine was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (47 mg, 89% yield) as a white solid. 1H NMR (CDCl3) δ 10.14 (s, 1 H), 8.47 (s, 1 H), 7.12-7.04 (m, 4 H), 7.00-6.96 (m, 2 H), 6.93-6.89 (m, 2 H), 6.74 (s, 1 H), 3.91 (s, 2 H), 3.86 (s, 3 H), 3.59 (m, 2 H), 3.51 (m, 2 H), 3.31 (s, 3 H); HRMS m/z calcd for C26H25FN3O5: 478.1773. Found: 478.1773.

Sources & evidence

ORD record: ord-8fd66664e81f438aa428e4bcacf0456a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

Loading…