Hydrochloric Acid → HCID 58317731, compound

HRID 2092885Notes

Reaction equation

HRID 2092885 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[C:7]([CH:13]=[N:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=2)[C:3]=1[C:4](O)=[O:5].[CH3:26][Li].Cl>C1COCC1>[Cl:1][C:2]1[C:3]2[C:4](=[O:5])[N:14]([CH2:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=3)[CH:13]([CH3:26])[C:7]=2[C:8]([F:12])=[C:9]([Cl:11])[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58317553HCID 58317553, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 58317731HCID 58317731, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2,6-dichloro-4-((3,5-dimethoxybenzylimino)methyl)-5-fluoronicotinic acid (5.8 g, 25.3 mmol) in THF (120 mL) was added methyl-lithium (60.0 mL, 126.6 mmol) drop wise at −78° C. After the addition was completed, the mixture was stirred for an additional 2 h. The reaction mixture was acidified with 1N HCl to pH 7 and THF was removed under reduced pressure. The mixture was extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4, and purified by silica gel chromatography eluting with PE-EtOAc (5:1) to give the title compound as a white solid (0.93 g, 16%). 1H-NMR (CDCl3, 400 MHz) δ 1.58 (d, J=6.8 Hz, 3H), 3.79 (s, 3H), 3.84 (s, 3H), 4.35 (d, J=14.4 Hz, 1H), 4.52 (q, J=6.8 Hz, 1H), 5.07 (d, J=14.4 Hz, 1H), 6.43-6.45 (m, 2H), 7.28 (d, J=9.2 Hz, 1H). [M+H] calc'd for C17H15Cl2FN2O3, 386. found, 385.

Workup

  1. additionAfter the addition
  2. customwas removed under reduced pressure
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by silica gel chromatography
  7. washeluting with PE-EtOAc (5:1)

Sources & evidence

ORD record
ord-61121e2f9c9a42b18dc15d448605e597
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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