Potassium Carbonate → HCID 23114812, compound

HRID 2080425Notes

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

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 61 was dissolved in a mixed solvent of acetic acid (2.0 ml) and water (2.0 ml). The resulting solution was heated to 60° C. and iron powder (40 mg, 0.72 mmol) was added thereto. The resulting 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 extract was washed with brine, dried and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (3% methanol/chloroform solution) to give the title compound (30 mg, 40%).

Workup

temperatureAfter cooling
extractionfollowed by extraction with ethyl acetate (60 ml)
washThe extract was washed with brine
customdried
concentrationconcentrated under reduced pressure
customThe residue thus obtained
customwas purified by silica gel chromatography (3% methanol/chloroform solution)

Sources & evidence

ORD record: ord-cd1afe5e25054bba8074c43ca4ce8d7f
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932271B2

Reaction notes

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