Ethanolamine → HCID 69480326, compound

HRID 2364364Notes

Reaction equation

HRID 2364364 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].[CH2:35]([CH2:37][NH2:38])[OH:36]>>[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:38][CH2:37][CH2:35][OH:36])=[O:29])[C:10]1=[O:33]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482671HCID 69482671, compound

Product 1

HCID 69480326HCID 69480326, 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 ethanolamine employing methods similar to those described in Example 202 and was obtained as an white solid. 1H NMR (400 MHz, CDCl3) δ 10.37 (t, J=5.3 Hz, 1 H), 8.59 (s, 1 H), 7.87 (s, 1 H), 7.24 (m, 2 H), 7.02 (t, J=8.6 Hz, 2 H), 4.42 (t, J=7.0 Hz, 2 H), 4.13 (s, 2 H), 3.87 (t, J=5.2 Hz, 2 H), 3.65 (m, 2 H), 3.36 (t, J=7.0 Hz, 2 H), 3.26 (t, J=6.5 Hz, 2 H), 3.08 (t, J=7.5 Hz, 2 H), 2.25 (m, 2 H); HRMS C23H25FN4O6S (M+H)+ calcd 505.1479, found 505.1558.

Workup

  1. customwas obtained as an white solid

Sources & evidence

ORD record
ord-30c7d4f4b253445f994b223a9aedd729
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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