1-Bromo-2-Chloroethane → HCID 59344699, compound

HRID 18002

Reaction equation

HRID 18002 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16](N(C)C)=[O:17])=[N:11][C:10]([OH:21])=[C:9]([OH:22])[C:8]=2[C:7]1=[O:23].C[O-:29].[Mg+2].C[O-].Br[CH2:34][CH2:35]Cl>CO.CS(C)=O.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:22])[C:10](=[O:21])[N:11]3[CH2:35][CH2:34][O:29][C:16](=[O:17])[C:12]3=2)[C:7]1=[O:23]

Participants

8

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 164537Methanol, magnesium salt (2:1)HCID 178484497HCID 178484497, compound

Product 1

HCID 59344699HCID 59344699, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent2×HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (0.15 g, 0.39 μmmol; Example 1, Step 9) and magnesium methoxide in methanol (2 mL, 6-10% methanol solution available from Aldrich) in DMSO (4 mL) was heated at 60° C. for 30 minutes. Methanol was exhaustively removed under vacuum over 45 minutes. The resultant DMSO solution was treated with 1-bromo-2-chloroethane (0.28 g, 1.97 mmol) and stirred at 60° C. under an atmosphere of nitrogen overnight. The reaction mixture was diluted with ethyl acetate and dilute hydrochloric acid. The organic extract was washed with aqueous sodium sulfite, brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by reverse phase high pressure liquid chromatography. Collection and lyophilization of appropriate fractions provided the title compound, which was recrystallized from a mixture of ethyl acetate and hexane

Workup

  1. customMethanol was exhaustively removed under vacuum over 45 minutes
  2. extractionThe organic extract
  3. washwas washed with aqueous sodium sulfite, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by reverse phase high pressure liquid chromatography
  8. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-bbf1e97e41e7415cb36be5abda3e68d2
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Linked notes

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