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

HRID 227128Notes

Reaction equation

HRID 227128 reaction equation
C(O[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:12][CH:13]=2)[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=2)[CH:7]=1)=[O:5])C.Cl.[CH3:30][NH:31][O:32][CH3:33].C[Al](C)C>C1(C)C=CC=CC=1>[CH3:33][O:32][N:31]([CH3:30])[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([C:17]([F:18])([F:20])[F:19])=[CH:12][CH:13]=2)[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=2)[CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 16682925TrimethylaluminumHCID 577545361-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Product 1

HCID 577547001-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (0.72 g, 1.6 mmol, 1 equiv) and methylmethoxyamine hydrochloride (0.16 g, 1 equiv) in 2 mL of toluene was treated with AlMe3 (0.5 M in toluene, 3.5 mL, 1.1 equiv) at rt for 1 h. The reaction was quenched by slow addition of saturated aqueous solution of sodium potassium tartrate. The organic layer was dried over sodium sulfate, filtered and evaporated to give crude 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3carboxylic acid methoxy-methyl-amide.

Workup

  1. customThe reaction was quenched by slow addition of saturated aqueous solution of sodium potassium tartrate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7335b073f5e842fd8cb88c5a19e7d7fb
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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