Pyridine → HCID 44553619, compound

HRID 1895918Notes

Reaction equation

HRID 1895918 reaction equation
[N:1]([CH2:4][CH3:5])=[C:2]=[O:3].[F:6][C:7]([F:26])([F:25])[C:8]1[CH:9]=[C:10]([S:14]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][NH2:24])[CH2:19][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:24][O:23][CH:20]1[CH2:21][CH2:22][N:17]([S:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([F:26])([F:6])[F:25])[CH:9]=2)(=[O:15])=[O:16])[CH2:18][CH2:19]1)=[O:3])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8022Ethyl isocyanateHCID 67118429O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

Product 1

HCID 44553619HCID 44553619, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isocyanatoethane (53.0 mg, 0.74 mmol) was added to a solution of O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (200 mg, 0.62 mmol) and pyridine (98 mg, 1.23 mmol) in CH2Cl2 (4 ml) and stirred at room temperature for 17 hours. The resulting precipitation was collected, washed with aqueous 1 N HCl solution (10 ml×3), aqueous NaHCO3 solution (10 ml×3), ether (10 ml×2) to give 1-ethyl-3-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)urea (156 mg, 64%) as a white solid: LCMS: 396 [M+1]+. 1H NMR (DMSO-d6) δ: 0.98 (m, 3H), 1.73 (m, 2H), 1.86 (m, 2H), 2.85 (m, 2H), 3.00 (m, 2H), 3.18 (n, 2H), 3.60 (m, 1H), 6.65 (m, 1H), 7.91 (m, 2H), 8.01 (m, 2H), 8.82 (s, 1H).

Workup

  1. customThe resulting precipitation
  2. customwas collected
  3. washwashed with aqueous 1 N HCl solution (10 ml×3), aqueous NaHCO3 solution (10 ml×3), ether (10 ml×2)

Sources & evidence

ORD record
ord-f99c8b6f5bbb4320a5a2c718dc78fa6e
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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