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

HRID 2364347Notes

Reaction equation

HRID 2364347 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][CH2:29][CH3:30])=[O:24])[C:5]1=[O:31].C(N(C(C)C)CC)(C)C.Cl[C:42]([O:44][CH3:45])=[O:43]>CN(C=O)C>[CH2:29]([O:28][CH2:27][CH2:26][NH:25][C:23]([C:6]1[C:5](=[O:31])[N:4]([CH2:3][CH2:2][NH:1][C:42](=[O:43])[O:44][CH3:45])[C:13]2[C:8]([C:7]=1[OH:22])=[N:9][CH:10]=[C:11]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH:12]=2)=[O:24])[CH3:30]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 694808831-(2-Aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 86612781Methyl {2-[3-({[2-(ethyloxy)ethyl]amino}carbonyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,5-naphthyridine-1(2H)-yl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.02 g, 0.047 mmol) and diisopropyl ethylamine (0.041 mL, 0.24 mmol) in DMF (5 mL) under nitrogen was treated with methyl chloroformate (0.0036 mL, 0.047 mmol) at ambient temperature. The reaction was concentrated in vacuo and the resulting residue treated with 1 N NaHSO4, filtered, then washed with 1 N NaHSO4 and Et2O before drying in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.1 (t, J=7.0 Hz, 3 H), 3.3 (m, 2 H), 3.4 (s, 3 H), 3.5 (m, 7 H), 4.1 (s, 2 H), 4.3 (t, J=6.0 Hz, 2 H), 7.1 (t, J=8.8 Hz, 2 H), 7.3 (m, 1 H), 7.4 (m, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 17.1 (s, 1 H); ES+ MS: 487 (M+H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe resulting residue treated with 1 N NaHSO4
  3. filtrationfiltered
  4. washwashed with 1 N NaHSO4 and Et2O
  5. custombefore drying in vacuo

Sources & evidence

ORD record
ord-3817395a13bf468db01b8f16dbb822b5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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