Potassium Carbonate → HCID 66652495, compound

HRID 2283632Notes

Reaction equation

[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:23])=[C:6]([S:8]([N:11]([CH2:19][O:20][CH2:21][CH3:22])[C:12]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.[NH2:25][C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=2[OH:39])[CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[NH2:25][C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=2[O:39][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([N:11]([CH2:19][O:20][CH2:21][CH3:22])[C:12]3[N:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=3)(=[O:10])=[O:9])=[C:5]([F:23])[CH:4]=2)[CH:29]=[CH:28][N:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-chloro-N-(ethoxymethyl)-2,4-difluoro-N-(5-fluoropyrimidin-2-yl)benzenesulfonamide (Preparation 14, 75 mg, 0.20 mmol) in dimethylsulfoxide (1 mL) was added 2-(2-aminopyridin-4-yl)-4-chlorophenol (Preparation 13, 43.3 mg, 0.20 mmol) and potassium carbonate (40.7 mg, 0.30 mmol). The reaction mixture was stirred at 50° C. for 19 hours, then diluted with ethyl acetate (30 mL) and washed with 1N aqueous sodium hydroxide solution, water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (50% hexanes in ethyl acetate to 100% ethyl acetate gradient elution) to afford the title compound as a white solid (68 mg).

Workup

washwashed with 1N aqueous sodium hydroxide solution, water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (50% hexanes in ethyl acetate to 100% ethyl acetate gradient elution)

Sources & evidence

ORD record: ord-21d0761abe5b49a291873028c41ee93c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145407B2

Reaction notes

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