Pyridine → HCID 86652734, compound

HRID 1895928Notes

Reaction equation

HRID 1895928 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[F:11][C:12]([F:32])([F:31])[O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]2[CH2:28][CH2:27][CH:26]([O:29][NH2:30])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:30][O:29][CH:26]2[CH2:25][CH2:24][N:23]([S:20]([C:17]3[CH:16]=[CH:15][C:14]([O:13][C:12]([F:32])([F:11])[F:31])=[CH:19][CH:18]=3)(=[O:21])=[O:22])[CH2:28][CH2:27]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 709554-Fluorophenyl isocyanateHCID 67118448HCID 67118448, compound

Product 1

HCID 86652734HCID 86652734, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Fluoro-4-isocyanatobenzene (96 mg, 0.70 mmol) was added to a solution of O-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yl) hydroxylamine (238 mg, 0.70 mmol) and pyridine (111 mg, 2.1 mmol) in CH2Cl2 (6 ml), and the whole was 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), diethyl ether (10 ml×2) to give 1-(4-fluorophenyl)-3-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-yloxy)urea (110 mg, 33%) as a white solid: LCMS: 478 [M+1]+. 1H NMR (DMSO-d6) δ: 1.81 (m, 2H), 1.92 (m, 2H), 2.85 (m, 2H), 3.22 (m, 2H), 3.78 (m, 1H), 7.10 (m, 2H), 7.51 (m, 2H), 7.65 (m, 2H), 7.91 (m, 2H), 8.62 (s, 1H), 9.38 (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), diethyl ether (10 ml×2)

Sources & evidence

ORD record
ord-9892f37e8e5f46b1964288e92914484a
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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