HCID 57942548, compound → HCID 57942484, compound

HRID 1438504Notes

Reaction equation

HRID 1438504 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH:25]3[CH3:30])=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32]>Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:15]2[C:16]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH:25]3[CH3:30])=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32]

Participants

4

Reactant 1

HCID 57942548HCID 57942548, compound

Product 1

HCID 57942484HCID 57942484, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4-chloro-N-[5-chloro-2-(3-methyl-morpholine-4-carbonyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (40 mg) in 3 mL HCl (4 M in dioxane) and water (1 mL) was refluxed for 2 h. Upon Cooling to room temperature, the mixture was concentrated and the residue was purified via preparative TLC (50% EtOAc in hexane) to afford 21 mg of 4-chloro-N[5-chloro-2-(3-methyl-morpholine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide as an off white solid. MS m/z: 498.0 (M+H).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified via preparative TLC (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-5a09ec9c7b2c48b68712e06ca5088f23
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

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