Hydrogen Bromide → HCID 178482454, compound

HRID 1817311Notes

Reaction equation

HRID 1817311 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[N:12][C:11]([OH:23])=[C:10]([O:24]C)[C:9]=3[C:8]2=[O:26])=[CH:4][CH:3]=1.Br.C(O)(=O)CC>C(Cl)Cl.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:19])=[O:20])=[N:12][C:11]([OH:23])=[C:10]([OH:24])[C:9]=3[C:8]2=[O:26])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 1032Propionic AcidHCID 178493935HCID 178493935, compound

Product 1

HCID 178482454HCID 178482454, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[6-(4-fluorobenzyl)-3-hydroxy-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide (0.0207 g, 0.506 mmol) in CH2Cl2 (6 mL) was added 30% by weight HBr in propionic acid (0.196 g HBr, 2.42 mmol). Alternatively, 30% HBr in acetic acid can be used. After 1.5 hours, the product mixture was evaporated and the residue partitioned between CHCl3 and 10% KHSO4. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum. The residual material was purified using reverse phase HPLC eluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to afford the title compound.

Workup

  1. customthe product mixture was evaporated
  2. customthe residue partitioned between CHCl3 and 10% KHSO4
  3. extractionThe organic extract
  4. dry with materialwas dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residual material was purified
  8. washeluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA)

Sources & evidence

ORD record
ord-b6d3358595bf4a8d9d34b2dfd33ca914
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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