Lithium Hydroxide → (S)-7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 1047163Notes

Reaction equation

HRID 1047163 reaction equation
[CH3:1][N:2]([CH3:31])[CH2:3][CH2:4][NH:5][C:6]1[N:15]=[C:14]2[C:9]([C:10](=[O:29])[C:11]([C:24]([O:26]CC)=[O:25])=[CH:12][N:13]2[CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[CH2:22][CH3:23])=[CH:8][C:7]=1[I:30].C1COCC1.[Li+].[OH-]>CO>[CH3:31][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]1[N:15]=[C:14]2[C:9]([C:10](=[O:29])[C:11]([C:24]([OH:26])=[O:25])=[CH:12][N:13]2[CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[CH2:22][CH3:23])=[CH:8][C:7]=1[I:30]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69621290(S)-ethyl 7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate2×

Product 1

HCID 68747399(S)-7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-ethyl 7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 40) was then taken up in methanol (2 mL) and THF (5 mL) and 1 ml of 2N LiOH was added and stirred at room temperature for 30 min. The solvent was removed in vacuo to give (S)-7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid as a light brown solid, material, which will be carried forward without further purification.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-29323c196fdb4734bde52029569d579c
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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