Acetic Acid → HCID 22346388, compound

HRID 897374Notes

Reaction equation

HRID 897374 reaction equation
CO[C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7]([Br:16])[N:6]=1)=[O:4].[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27].C(N(CC)CC)C.C(O)(=O)C>CCO.CN(C=O)C.O>[Br:16][C:7]1[N:6]=[C:5]([C:3]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[S:26]([N:29]([CH3:31])[CH3:30])(=[O:27])=[O:28])=[O:4])[C:14]([OH:15])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 16753952HCID 16753952, compoundHCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 22346388HCID 22346388, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylic acid methyl ester (1.00 g, 3.53 mmol, see Example 113), 2-(aminomethyl)-5-fluoro-N,N-dimethylbenzenesulfonamide (1.64 g, 7.07 mmol), and triethylamine (0.99 mL, 7.07 mmol) in EtOH (8 mL) and DMF (2 mL) was heated to 78° C. overnight. The mixture was cooled to 40° C. and glacial acetic acid (0.81 mL, 14.1 mmol) was added. The mixture was allowed to cool to room temperature and water was added dropwise while sonicating to facilitate the product precipitating out of solution. The solids were collected by vacuum filtration to afford the desired product as a light yellow solid.

Workup

  1. temperatureThe mixture was cooled to 40° C.
  2. temperatureto cool to room temperature
  3. customwhile sonicating
  4. customprecipitating out of solution
  5. filtrationThe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-37942bb80a234eb58aab379bf1569272
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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