Triethylamine → 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide

HRID 227026Notes

Reaction equation

HRID 227026 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]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20]([OH:22])=O)=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>O.C(#N)C>[CH3:27][O:26][N:25]([CH3:24])[C:20]([C:11]1[C:12](=[O:19])[C:13]2[C:18](=[CH:17][CH:16]=[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

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 111923Propylphosphonic anhydrideHCID 577547691-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Product 1

HCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

9.45 g (26.3 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 2.82 g (28.9 mmol) of N,O-dimethylhydroxylamine hydrochloride, 22 mL (16 g, 158 mmol) of triethylamine and 18.8 mL (20.1 g, 31.6 mmol) of 50% 1-propanephosphonic acid cyclic anhydride were sequentially added to 250 mL acetonitrile at rt. After 1 h 400 mL of water were added and the mixture was extracted two times with 300 mL DCM. Combined organic layers were evaporated and the residue purified on silica flash column using 0-15% methanol in EtOAc to give 9.62 g of the product as an off-white solid.

Workup

  1. extractionthe mixture was extracted two times with 300 mL DCM
  2. customCombined organic layers were evaporated
  3. customthe residue purified on silica flash column

Sources & evidence

ORD record
ord-9545d53462e94db7a3fe24c4105ca0f1
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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