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

HRID 1867935Notes

Reaction equation

HRID 1867935 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.C([N:33]([CH:36]([CH3:38])[CH3:37])[CH2:34]C)(C)C.[OH2:39]>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:33]3[CH2:34][CH2:38][C@H:36]3[CH2:37][OH:39])[N:11]=2)[C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8]1

Participants

5

Reactant 3

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

Product 1

HCID 69026965Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-(s)-hydroxymethyl-azetidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of EXAMPLE 1B (1.6 g), (S)-(2-hydroxymethyl)azetidine hydrochloride (660 mg), and diisopropylethylamine (4 mL) in acetonitrile (25 mL) at 25° C. was stirred for 3.5 days, treated with water, and filtered. The filtrant was flash chromatographed on silica gel with 9:1 dichloromethane/methanol.

Workup

  1. filtrationfiltered
  2. customchromatographed on silica gel with 9:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-437f736ff63743348067c80cffed08ef
Source dataset
uspto-grants-2009_12
Patent number
US07632946B2

Reaction notes

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