Water → 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide

HRID 226988Notes

Reaction equation

HRID 226988 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[N:17]=3)[C:12](=[O:20])[C:11]([C:21](O)=[O:22])=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.[CH3:24][NH:25][O:26][CH3:27].C(N(C(C)C)CC)(C)C.O>ClCCl>[CH3:27][O:26][N:25]([CH3:24])[C:21]([C:11]1[C:12](=[O:20])[C:13]2[C:18](=[N:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)[CH:10]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 577547571-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 577545251-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.667 mL (3.75 mmol, 50% solution in ethyl acetate) of 1-propanephosphonic anhydride solution was added to 0.400 g (1.07 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid, 0.208 g (2.13 mmol) of N,O-dimethylhydroxyl amine, and 0.653 mL (3.75 mmol) of diisopropylethylamine dissolved in 1 mL of dichloromethane. After the reaction was stirred at room temperature for 1 hour water was added and was extracted with dichloromethane (3×25 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel eluting with 100% ethyl acetate to yield 0.355 g of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide as a white solid.

Workup

  1. additionwas added
  2. extractionwas extracted with dichloromethane (3×25 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified on silica gel eluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-2241ea9a5d8c4f808f01df860393bc2a
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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