Water → Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-(s)-hydroxymethyl-pyrrolidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate

HRID 1867930Notes

Reaction equation

HRID 1867930 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1F.[NH:30]1[CH2:36][CH2:35][CH2:34][C@H:31]1[CH2:32][OH:33].C(N(C(C)C)CC)(C)C.O>C(#N)C>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([N:30]3[CH2:36][CH2:35][CH2:34][C@H:31]3[CH2:32][OH:33])[N:11]=2)[C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 13937202Ethyl 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 69029517Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-(s)-hydroxymethyl-pyrrolidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of EXAMPLE 1B (2.96 g), (S)-prolinol (850 μL), and diisopropylethylamine (4 mL) in acetonitrile (70 mL) at 25° C. was stirred for 3 days, treated with water, and extracted with dichloromethane. The extract was washed with 1M hydrochloric acid, water, saturated NaHCO3, and water, and concentrated.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with 1M hydrochloric acid, water, saturated NaHCO3, and water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-730cb9642d1c4cd0958e6d6f3aefa9d7
Source dataset
uspto-grants-2009_12
Patent number
US07632946B2

Reaction notes

Loading…