4-Morpholinecarbonyl chloride → HCID 69481537, compound

HRID 2364467Notes

Reaction equation

HRID 2364467 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][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28])=[O:24])[C:5]1=[O:31].[N:32]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]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][C:26]([CH3:29])([CH3:30])[CH2:27][OH:28])=[O:24])[C:5](=[O:31])[N:4]3[CH2:3][CH2:2][NH:1][C:38]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:39])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 69480357HCID 69480357, compound

Product 1

HCID 69481537HCID 69481537, compound

Procedure

This compound was prepared from 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1,1-dimethylethyl)-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 orange solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.36 (s, 6 H), 2.03 (s, 1 H), 3.13-3.20 (m, 4 H), 3.27-3.30 (m, 2 H), 3.48 (dt, J=4.56, 2.35 Hz, 6 H), 4.13 (s, 2 H), 4.27 (t, J=6.04 Hz, 2 H), 5.09-5.15 (m, 1 H), 6.75 (t, J=5.76 Hz, 1 H), 7.10-7.18 (m, 2.04 Hz, 2 H), 7.39-7.44 (m, 2 H), 8.23 (d, J=1.54 Hz, 1 H), 8.53 (d, J=1.26 Hz, 1 H), 10.53 (s, 1 H); ES+ MS: 542 (M+H+).

Workup

  1. customwas obtained as an orange solid

Sources & evidence

ORD record
ord-303b7180d45849bb861b25a3be104cee
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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