Hydrochloric Acid → HCID 56592442, compound

HRID 2359266Notes

Reaction equation

HRID 2359266 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].CCN=C=NCCCN(C)C.Cl.[CH3:36][S:37]([NH2:40])(=[O:39])=[O:38].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58046311HCID 58046311, compound

Product 1

HCID 56592442HCID 56592442, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-chloro-4-(4-chloro-3-(trifluoromethyl)phenoxy)-2-fluorobenzoic acid (Preparation 32, 219 mg, 0.58 mmol) in DCM (3 mL) were added EDCl (167 mg, 0.87 mmol) and DMAP (106 mg, 0.87 mmol) and the reaction stirred at room temperature for 30 minutes. Methanesulfonamide (83 mg, 0.87 mmol) was added and the stirring continued at room temperature for 16 hours. DCM (25 mL) and 2M aq. HCl (5 mL) were added and the two layers separated. The organic extract was washed with 2M aq. HCl (5 mL) and brine (10 mL), dried (MgSO4), filtered and the solvent removed in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc:heptane:AcOH (50:50:0.5), followed by recrystallisation from hot IPA to yield the title compound (89 mg, 34%) as a white solid.

Workup

  1. waitthe stirring continued at room temperature for 16 hours
  2. customthe two layers separated
  3. extractionThe organic extract
  4. washwas washed with 2M aq. HCl (5 mL) and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude material was purified by silica gel column chromatography
  9. washeluting with EtOAc:heptane:AcOH (50:50:0.5)
  10. customfollowed by recrystallisation from hot IPA

Sources & evidence

ORD record
ord-3059357d8a354367a585fa59527ccfef
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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