2-Methoxyethylamine → HCID 69480406, compound

HRID 2364434Notes

Reaction equation

HRID 2364434 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26](OCC)=[O:27])[C:8]2=[O:31])[CH2:3][CH2:2]1.[CH3:33][O:34][CH2:35][CH2:36][NH2:37]>>[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26]([NH:37][CH2:36][CH2:35][O:34][CH3:33])=[O:27])[C:8]2=[O:31])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 69482711HCID 69482711, compound

Product 1

HCID 69480406HCID 69480406, compound

Procedure

This compound was prepared from ethyl 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine by methods similar to those described in Example 245. The crude material was triturated with a mixture of MeOH and 1N HCl to afford the product as a white solid: 1H NMR (d6-DMSO) δ 10.22 (1H, br), 8.54 (1H, br s), 8.24 (1H, br s), 7.74 (1H, br s), 7.32 (2H, m), 7.11 (2H, m), 4.80 (2H, s), 4.11 (2H, s), 3.51 (4H, m), 3.27 (3H, s), 2.56 (1H, m), 0.59 (2H, m), 0.34 (2H, m); HRMS calcd for C24H25FN4O5+H+: 469.1887. Found: 469.1882.

Workup

  1. customThe crude material was triturated with a mixture of MeOH and 1N HCl

Sources & evidence

ORD record
ord-77e7e35b13f14a1ebaa2711932c34b39
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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