Water → Methyl {2-[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-{[(2-hydroxyethyl)amino]carbonyl}-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

HRID 2364342Notes

Reaction equation

HRID 2364342 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][OH:28])=[O:24])[C:5]1=[O:29].C(N(C(C)C)CC)(C)C.Cl[C:40]([O:42][CH3:43])=[O:41].O>CN(C=O)C>[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][OH:28])=[O:24])[C:5](=[O:29])[N:4]3[CH2:3][CH2:2][NH:1][C:40](=[O:41])[O:42][CH3:43])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 694804131-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 86762321Methyl {2-[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-{[(2-hydroxyethyl)amino]carbonyl}-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.0207 g, 0.052 mmol) and diisopropyl ethylamine (0.075 mL, 0.43 mmol) in DMF (2 mL) under nitrogen was treated with methyl chloroformate (0.0038 mL, 0.049 mmol) at ambient temperature. Water was added (2 mL) and the reaction was concentrated in vacuo. The resulting residue was purified by reversed phase HPLC to provide the title compound from pure fraction concentrated in vacuo as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 3.2 (m, 2 H), 3.4 (m, 5 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.3 (t, J=6.3 Hz, 2 H), 4.9 (t, J=4.9 Hz, 1 H), 7.1 (t, J=8.9 Hz, 2 H), 7.3 (t, J=6.0 Hz, 1 H), 7.4 (m, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.4 (m, 1 H); ES+ MS: 459 (M+H+).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe resulting residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-1944f9cff138463ab84fad4f2a69a8ea
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…