Pyridine → HCID 58235348, compound

HRID 1895939Notes

Reaction equation

HRID 1895939 reaction equation
[N:1]([CH2:4][CH3:5])=[C:2]=[O:3].[F:6][C:7]([F:25])([F:24])[C:8]1[CH:9]=[C:10]([S:14]([N:17]2[CH2:21][CH2:20][C@H:19]([O:22][NH2:23])[CH2:18]2)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:4]([NH:1][C:2]([NH:23][O:22][C@H:19]1[CH2:20][CH2:21][N:17]([S:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([F:25])([F:6])[F:24])[CH:9]=2)(=[O:15])=[O:16])[CH2:18]1)=[O:3])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8022Ethyl isocyanateHCID 67118437HCID 67118437, compound

Product 1

HCID 58235348HCID 58235348, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isocyanatoethane (36.0 mg, 0.5 mmol) was added to a solution of (S)—O-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yl)hydroxyl amine (155 mg, 0.5 mmol) and pyridine (119 mg, 1.5 mmol) in CH2Cl2 (8 ml), and the whole was stirred at room temperature for 17 hours. The reaction mixture was washed with aqueous 0.1 N HCl solution (10 ml), H2O (20 ml×3) and brine (20 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 60/40) to give (S)-1-ethyl-3-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yloxy)urea (150 mg, 64%) as pale yellow oil: LCMS: 382 [M+1]+. 1H NMR (DMSO-d6) δ: 0.95-1.00 (3H, t), 1.74-1.84 (1H, M), 2.05-2.06 (1H, m), 2.99-3.04 (2H, m), 3.15-3.31 (3H, m), 3.50-3.54 (1H, d), 4.21 (1H, s), 6.66-6.70 (1H, t), 7.84-7.89 (1H, t), 8.01 (1H, s), 8.07-8.14 (1H, t), 8.92 (1H, s).

Workup

  1. washThe reaction mixture was washed with aqueous 0.1 N HCl solution (10 ml), H2O (20 ml×3) and brine (20 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate/petroleum ether: 60/40)

Sources & evidence

ORD record
ord-1a2190de37b94a04a55a7abcf994b22e
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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