4-Morpholinecarbonyl chloride → HCID 69482557, compound

HRID 2364466Notes

Reaction equation

HRID 2364466 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][CH:26]([CH2:30][OH:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[C:5]1=[O:32].[N:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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][CH:26]([CH2:30][OH:31])[CH:27]([CH3:29])[CH3:28])=[O:24])[C:5](=[O:32])[N:4]3[CH2:3][CH2:2][NH:1][C:39]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[O:40])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 69482469HCID 69482469, compound

Product 1

HCID 69482557HCID 69482557, compound

Procedure

This compound was prepared from 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[1-(hydroxymethyl)-2-methylpropyl]-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 0.88-0.96 (m, 6 H), 1.92-2.04 (m, 2 H), 3.12-3.21 (m, 4 H), 3.27-3.31 (m, 2 H), 3.44-3.51 (m, 5 H), 3.51-3.61 (m, 1 H), 3.86 (ddd, J=14.64, 5.30, 5.19 Hz, 1 H), 4.14 (s, 2 H), 4.29 (t, J=6.25 Hz, 2 H), 4.88 (t, J=5.05 Hz, 1 H), 6.77 (t, J=5.76 Hz, 1 H), 7.11-7.18 (m, 2 H), 7.39-7.45 (m, 2 H), 8.25 (d, J=1.54 Hz, 1 H), 8.54 (d, J=0.98 Hz, 1 H), 10.44 (d, J=9.13 Hz, 1 H); ES+ MS: 556 (M+H+).

Workup

  1. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-6cde6743d0d04fdb92464485437c2a36
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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