Chlorosuccinimide → HCID 118036739, compound

HRID 1777855Notes

Reaction equation

HRID 1777855 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1.[Cl:16]N1C(=O)CCC1=O>CC#N>[Cl:16][C:5]1[CH:6]=[C:7]2[C:12](=[N:13][C:4]=1[CH:3]([O:2][CH3:1])[O:14][CH3:15])[NH:11][CH2:10][CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 177501767-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine2×

Product 1

HCID 118036739HCID 118036739, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 4, 200 mg, 0.960 mmol) in MeCN (5 ml) was treated with N-chlorosuccinimide (145 mg, 1.086 mmol), stirred for 20 h. The reaction mixture was concentrated; the residue was treated with Et2O and EtOAc, washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) the product containing fractions were concentrated. The residue was dissolved in EtOAc, washed twice water (2×) and brine, dried over Na2SO4, filtered and concentrated to give the title compound as a pale yellow oil. (UPLC-MS 1) tR 0.68 min; ESI-MS 243.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was treated with Et2O and EtOAc
  3. washwashed with water (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) the product
  8. additioncontaining fractions
  9. concentrationwere concentrated
  10. dissolutionThe residue was dissolved in EtOAc
  11. washwashed twice water (2×) and brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-4287efa2c633416eb530d4cfa25b97da
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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