Triethylamine → HCID 59375579, compound

HRID 2192975Notes

Reaction equation

HRID 2192975 reaction equation
FC(F)(F)C([O-])=O.[CH3:8][C@@H:9]([NH:13][C:14]1[C:23]2[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=2[C:21]2[C:20](=[O:29])[NH:19][CH:18]=[CH:17][C:16]=2[NH+:15]=1)[CH:10]([CH3:12])[CH3:11].C(N(CC)CC)C.[Br:37]NC(=O)CCC(N)=O>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:37][C:17]1[C:16]2[N:15]=[C:14]([NH:13][C@H:9]([CH3:8])[CH:10]([CH3:11])[CH3:12])[C:23]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=3[C:21]=2[C:20](=[O:29])[NH:19][CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 9834204N-BromosuccinamideHCID 67416131HCID 67416131, compound

Product 1

HCID 59375579HCID 59375579, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-{[(1R)-1,2-dimethylpropyl]amino}-9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-5-ium trifluoroacetate (53 mg, 0.13 mmol) in DMF (3 mL) were added triethylamine (18 uL, 0.13 mmol) and N-bromosuccinamide (27 mg, 0.15 mmol). The solution was stirred for 2 hr then diluted with EtOAc and sat. NaHCO3. The organic layers were separated, dried with MgSO4, filtered, and concentrated. The resulting crude mixture was purified by silica column chromatography 100% Hex. to 100% EtOAC to afford 4-bromo-6-{[(1R)-1,2-dimethylpropyl]amino}-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 9.55 (d, 1H), 8.37 (m, 1H), 7.66 (s, 1H), 7.36 (m, 1H), 4.65 (m, 1H), 2.1 (m, 1H) 1.30 (d, 3H), 1.0 (m, 6H). LRMS (ESI) calc'd for (C17H18Br2FN3O) [M+H]+, 378.1; found 378.0.

Workup

  1. customThe organic layers were separated
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude mixture was purified by silica column chromatography 100% Hex

Sources & evidence

ORD record
ord-9283b6c5ba224676ac78a2097777b660
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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