Potassium Carbonate → HCID 23114812, compound

HRID 748859Notes

Reaction equation

HRID 748859 reaction equation
[Cl:1][C:2]1[C:3]([CH:18]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])=[CH:4][C:5]([NH:8][CH2:9][CH2:10][N+:11]2([O-])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([CH:18]([S:27]([C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)(=[O:28])=[O:29])[C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])=[CH:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 23114841HCID 23114841, compound

Product 1

HCID 23114812HCID 23114812, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The 4-[2-[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-2-yl]aminoethyl]morpholine-N-oxide (78 mg, 0.14 mmol) obtained in Example 349 was dissolved in a mixed solvent of acetic acid (2.0 ml) and water (2.0 ml). The resulting mixture was heated to 60° C. Iron powder (40 mg, 0.72 mmol) was added and the mixture was stirred for 30 minutes. After cooling, the reaction mixture was poured into a saturated aqueous solution of potassium carbonate, followed by extraction with ethyl acetate (60 ml). The solution was washed with brine, dried and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (3% methanol/chloroform solution), whereby the title compound (30 mg, 40%) was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate (60 ml)
  3. washThe solution was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (3% methanol/chloroform solution), whereby the title compound (30 mg, 40%)
  7. customwas obtained

Sources & evidence

ORD record
ord-8a6b9c1bee144a81bb0f1d277dc5f32d
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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