1,3-Dibromo-5,5-dimethylhydantoin → Ethyl 7-azetidin-1-yl-6-bromo-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696939Notes

Reaction equation

HRID 1696939 reaction equation
[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:24])[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][N:12]3[CH2:15][CH2:16][C:17]#[N:18])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[Br:25]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)Cl>[N:1]1([C:5]2[N:14]=[C:13]3[C:8]([C:9](=[O:24])[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][N:12]3[CH2:15][CH2:16][C:17]#[N:18])=[CH:7][C:6]=2[Br:25])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 67275510Ethyl 7-azetidin-1-yl-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67275613Ethyl 7-azetidin-1-yl-6-bromo-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of EXAMPLE 81C (0.50 g) and 1,3-dibromo-5,5-dimethylhydantoin (0.26 g) in chloroform (100 mL) was refluxed for 10 minutes then cooled, diluted with chloroform, washed with 10% sodium bisulfate and brine, dried (MgSO4), filtered, and concentrated; and the concentrate was crystallized from dichloromethane/ethyl acetate/hexanes.

Workup

  1. temperaturethen cooled
  2. washwashed with 10% sodium bisulfate and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customand the concentrate was crystallized from dichloromethane/ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2c53c91670054f589f5accb41e7e45ba
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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