4-Morpholinecarbonyl chloride → HCID 69650856, compound

HRID 2364463Notes

Reaction equation

HRID 2364463 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH3:29])=[O:24])[C:5]1=[O:30].[N:31]1([C:37](Cl)=[O:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:11]2[CH:12]=[C:13]3[C:8]([C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH3:29])=[O:24])[C:5](=[O:30])[N:4]3[CH2:3][CH2:2][NH:1][C:37]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:38])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 694803851-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 69650856HCID 69650856, compound

Procedure

This compound was prepared from 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide and 4-morpholinecarbonyl chloride employing methods similar to those described in Example 450 and was obtained as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.72 (s, 1 H), 3.13-3.20 (m, 3 H), 3.31 (s, 4 H), 3.45-3.50 (m, 5 H), 3.50-3.58 (m, 5 H), 4.13 (s, 2 H), 4.28 (t, J=6.39 Hz, 2 H), 6.77 (t, J=5.40 Hz, 1 H), 7.14 (t, J=8.84 Hz, 2 H), 7.41 (dd, J=8.49, 5.55 Hz, 2 H), 8.26 (s, 1 H), 8.55 (d, J=0.70 Hz, 1 H), 10.42 (t, J=5.62 Hz, 1 H); ES+ MS: 528 (M+H+).

Workup

  1. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-5335c7c25afa4f62bb29839dc28993de
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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