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

HRID 1867932Notes

Reaction equation

HRID 1867932 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 2724541Prolinol, (R)-HCID 13937202Ethyl 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 69028368Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-(r)-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), (R)-prolinol (850 μL) and diisopropylethylamine (4 mL) in acetonitrile (70 mL) at 25° C. was stirred for 3 days, treated with water, and filtered.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-2daf1db0f1304357b1e5b09f9a8f3488
Source dataset
uspto-grants-2009_12
Patent number
US07632946B2

Reaction notes

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