Ethanol → HCID 69480931, compound

HRID 2364350Notes

Reaction equation

HRID 2364350 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].[CH:30]([N:33]([CH:36](C)C)[CH2:34]C)(C)C.CC[OH:41]>CN(C=O)C>[CH3:30][N:33]([CH3:36])[C:34]([NH: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:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=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])=[O:41]

Participants

5

Reactant 3

HCID 702EthanolHCID 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 69480931HCID 69480931, compound

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 (0.019 g, 0.047 mmol) and diisopropyl ethylamine (0.15 mL, 0.86 mmol) in DMF (1.2 mL) under nitrogen was treated with N,N-dimethyl carbonyl chloride (0.0038 mL, 0.041 mmol) at ambient temperature. After 2 h, added EtOH (0.25 mL) and concentrated in vacuo. The resulting residue suspended in 1 N NaHSO4 the refrigerated overnight. 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 2.7 (s, 6 H), 3.3 (s, 4 H), 3.4 (t, J=5.5 Hz, 2 H), 3.6 (t, J=5.3 Hz, 2 H), 4.1 (s, 2 H), 4.2 (t, J=6.0 Hz, 2 H), 4.9 (m, 1 H), 6.5 (m, 1 H), 7.1 (t, J=8.9 Hz, 2 H), 7.4 (m, 2 H), 8.3 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES− MS: 472 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe refrigerated overnight
  3. customPurified by reversed phase HPLC

Sources & evidence

ORD record
ord-e4acc82e82f140a3906894c0309ec1d6
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…