2-Methoxyethylamine → HCID 69483254, compound

HRID 2364373Notes

Reaction equation

HRID 2364373 reaction equation
[O:1]=[S:2]1(=[O:34])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][N:9]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=2)[C:12]([OH:27])=[C:11]([C:28](OCC)=[O:29])[C:10]1=[O:33].[CH3:35][O:36][CH2:37][CH2:38][NH2:39]>>[O:34]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][N:9]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=2)[C:12]([OH:27])=[C:11]([C:28]([NH:39][CH2:38][CH2:37][O:36][CH3:35])=[O:29])[C:10]1=[O:33]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 69482671HCID 69482671, compound

Product 1

HCID 69483254HCID 69483254, compound

Procedure

This compound was prepared from ethyl 1-[2-(1, 1-dioxido-2-isothiazolidinyl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-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 10.24 (s, 1 H), 8.58 (s, 1 H), 7.86 (s, 1 H), 7.24 (m, 2 H), 7.01 (t, J=8.6 Hz, 2 H), 4.42 (t, J=7.0 Hz, 2 H), 4.12 (s, 2 H), 3.65 (m, 2 H), 3.59 (m, 2 H), 3.42 (s, 3 H), 3.36 (t, J=6.9 Hz, 2 H), 3.26 (t, J=6.7 Hz, 2 H), 3.07 (t, J=7.5 Hz, 2 H), 2.24 (m, 2 H); HRMS C24H27FN4O6S (M+H)+ calcd 519.1635, found 519.1718.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-6749d0d5da30494b9e87798819cd27f5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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