2-Methoxyethylamine → HCID 69480473, compound

HRID 2364285Notes

Reaction equation

HRID 2364285 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:27](OCC)=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[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:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:32])=[C:14]([C:27]([NH:37][CH2:36][CH2:35][O:34][CH3:33])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 69480155HCID 69480155, compound

Product 1

HCID 69480473HCID 69480473, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfonyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to those described in Example 202 and was obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.22 (s, 1 H), 8.57 (s, 1 H), 7.67 (s, 1 H), 7.21 (dd, J=8.6, 5.5 Hz, 2 H), 7.01 (t, J=8.7 Hz, 2 H), 4.39 (t, J=7.8 Hz, 2 H), 4.12 (s, 2 H), 3.65 (m, 2 H), 3.59 (m, 2 H), 3.41 (s, 3 H), 3.14 (t, J=7.0 Hz, 2 H), 2.95 (s, 3 H), 2.21 (m, 2 H); HRMS C23H26FN3O6S (M+H)+ calcd 492.1526, found 492.1603.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-6379a9cabc1a4e8f99865bb4cb318f26
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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