Acetone → Sodium 5-(1,1-dioxido-1,2-thiazinan-2-yl)-7-[({4-fluoro-2-[(methylamino)carbonyl]benzyl}amino)carbonyl]-1,6-naphthyridin-8-olate

HRID 2252805Notes

Reaction equation

HRID 2252805 reaction equation
[OH-].[Na+:2].[O:3]=[S:4]1(=[O:36])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[N:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[C:31]([NH:33][CH3:34])=[O:32])=[O:21])[C:17]([OH:35])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.CC(C)=O.C(#N)C>O>[O:36]=[S:4]1(=[O:3])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[N:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[C:31]([NH:33][CH3:34])=[O:32])=[O:21])[C:17]([O-:35])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.[Na+:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 30133965-(1,1-dioxothiazinan-2-yl)-N-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 69180949Sodium 5-(1,1-dioxido-1,2-thiazinan-2-yl)-7-[({4-fluoro-2-[(methylamino)carbonyl]benzyl}amino)carbonyl]-1,6-naphthyridin-8-olate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (150 μL, 0.15 mmol, 1N solution) was added to a cloudy solution of 5-(1,1-dioxido-1,2-thiazinan-2-yl)-N-{4-fluoro-2-[(methylamino)carbonyl]benzyl}-8-hydroxy-1,6-naphthyridine-7-carboxamide (73 mg, 0.15 mmol) in a 2 mL mixture of acetone, acetonitrile and water. The homogeneous bright yellow solution was allowed to stir at room temperature for 30 minutes. The solvent was removed in vacuo and dried overnight on the high vac with gentle heating to give the desired product as a bright yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customdried overnight on the high vac
  3. temperaturewith gentle heating

Sources & evidence

ORD record
ord-d64a7d43a37143dfacef00793149710a
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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