Hydrochloric Acid → N-[4-fluoro-2-(methylsulfonyl)benzyl]-4-hydroxy-1-[2-(methylamino)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 1179319Notes

Reaction equation

HRID 1179319 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:35])[N:12]([CH2:21][CH2:22][N:23](C)[C:24](=O)OCC3C=CC=CC=3)[C:13]3[C:18]([C:19]=2[OH:20])=[N:17][CH:16]=[CH:15][CH:14]=3)=[O:9])=[C:4]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:3]=1.Cl>CO>[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:35])[N:12]([CH2:21][CH2:22][NH:23][CH3:24])[C:13]3[C:18]([C:19]=2[OH:20])=[N:17][CH:16]=[CH:15][CH:14]=3)=[O:9])=[C:4]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58977990benzyl 2-[3-({[4-fluoro-2-(methylsulfonyl)benzyl]amino}carbonyl)-4-hydroxy-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl(methyl)carbamate

Product 1

HCID 58978004N-[4-fluoro-2-(methylsulfonyl)benzyl]-4-hydroxy-1-[2-(methylamino)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl 2-[3-({[4-fluoro-2-(methylsulfonyl)benzyl]amino}carbonyl)-4-hydroxy-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl(methyl)carbamate (0.55 g, 0.94 mmol) in MeOH (10 mL) in a pressure tube was cooled to −78 degrees C. and saturated with HCl gas. The volume in the flask visibly increased. The reaction was allowed to warm to room temperature overnight, then cooled to −78 degrees C. and vented. The reaction was transferred to a round bottom flask and the solvents removed under vacuum. The reaction was suspended in toluene and evaporated to give the product as a solid.

Workup

  1. temperatureThe volume in the flask visibly increased
  2. temperaturecooled to −78 degrees C
  3. customThe reaction was transferred to a round bottom flask
  4. customthe solvents removed under vacuum
  5. customevaporated

Sources & evidence

ORD record
ord-936671a134764351b84046b62ac37375
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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