Potassium Carbonate → HCID 86652738, compound

HRID 1895934Notes

Reaction equation

HRID 1895934 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([S:9](Cl)(=[O:11])=[O:10])[CH2:5][CH2:4]1.Cl.[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:23])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>O.O1CCOCC1>[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][O:25][CH:26]2[CH2:31][CH2:30][N:29]([S:9]([N:6]3[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]3)(=[O:11])=[O:10])[CH2:28][CH2:27]2)=[O:23])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 187987054-Methylpiperazine-1-sulfonyl chloride--hydrogen chloride (1/1)HCID 86652736HCID 86652736, compound

Product 1

HCID 86652738HCID 86652738, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

4-Methylpiperazine-1-sulfonyl chloride hydrochloride (227 mg, 0.966 mmol) was added at room temperature to a solution of 1-(4-fluorophenyl)-3-(piperidin-4-yloxy)urea hydrochloride (140 mg, 0.483 mmol) and K2CO3 (200 mg, 1.45 mmol) in H2O-dioxane (1:1, 4 ml), and the whole was stirred at room temperature for 18 hours. The reaction was quenched with K2CO3 (200 mg) in H2O (10 ml), extracted with ethyl acetate (20 ml×3). The combined organic layer was washed with brine (10 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (chloroform/methanol: 90/10) to give 1-(4-fluorophenyl)-3-(1-(4-methylpiperazin-1-ylsulfonyl)piperidin-4-yloxy)urea (139 mg, 69%) as pale yellow amorphous: LCMS: 416 [M+1]+. 1H NMR (DMSO-d6) δ: 1.72 (m, 2H), 1.93 (m, 2H), 2.19 (s, 3H), 2.35 (m, 4H), 3.01-3.13 (m, 6H), 3.45 (m, 2H), 3.85 (m, 1H), 7.11 (m, 2H), 7.55 (m, 2H), 8.68 (s, 1H), 9.45 (s, 1H).

Workup

  1. customThe reaction was quenched with K2CO3 (200 mg) in H2O (10 ml)
  2. extractionextracted with ethyl acetate (20 ml×3)
  3. washThe combined organic layer was washed with brine (10 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (chloroform/methanol: 90/10)

Sources & evidence

ORD record
ord-5b8b504af56c4d7cbd2099455d3b1cd1
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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