HCID 178498360, compound → Halauxifen-methyl

HRID 889660Notes

Reaction equation

HRID 889660 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH3:26])[C:19]=2[F:27])[CH2:8]/[C:9](=[N:12]\OS(C)(=O)=O)/[C:10]=1[Cl:11])=[O:4]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([NH2:12])[CH:8]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH3:26])[C:19]=2[F:27])[N:6]=1)=[O:4]

Participants

3

Reactant 1

HCID 178498360HCID 178498360, compound

Product 1

HCID 16656802Halauxifen-methyl

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A magnetically stirred solution of 6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-[(E)-methanesulfonyloximino]-3-chloro-1,4,5,6-tetrahydropyridine-2-carboxylic acid methyl ester (29, 0.441 g (0.001 mol) in glacial acetic acid (2 mL) was warmed to 90° C. for 4 h. After removing the solvent on the rotary evaporator, the residue was dissolved in CH2Cl2 (25 mL) and was washed with saturated solutions of NaHCO3 and NaCl. After drying (MgSO4), solvent removal gave 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid methyl ester (39; 0.332 g, 96%; 93% pure by GC and 1H NMR spectroscopy) as a white solid: mp 141-143° C. 1H NMR (400 MHz, CDCl3) δ 7.65 (dd, J=8.6, 7.8 Hz, 1H), 7.23 (dd, J=8.7, 1.8 Hz, 1H), 7.18 (d, J=1.7 Hz, 1H), 4.85 (s, 2H), 4.00 (s, 3H), 3.97 (d, J=0.9 Hz, 3H). HRMS-ESI (m/z): calcd for C14H11Cl2FN2O3, 344.013. found, 344.013.

Workup

  1. customAfter removing the solvent
  2. customon the rotary evaporator
  3. dissolutionthe residue was dissolved in CH2Cl2 (25 mL)
  4. washwas washed with saturated solutions of NaHCO3 and NaCl
  5. customAfter drying
  6. custom(MgSO4), solvent removal

Sources & evidence

ORD record
ord-49eafc0dba5c4940a9e43538ab68cf08
Source dataset
uspto-grants-2012_08
Patent number
US08252938B2

Reaction notes

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