Propylamine → HCID 58235432, compound

HRID 1895940Notes

Reaction equation

HRID 1895940 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1C=CN=C1)=[O:2].[F:13][C:14]([F:32])([F:31])[C:15]1[CH:16]=[C:17]([S:21]([N:24]2[CH2:28][CH2:27][C@H:26]([O:29]N)[CH2:25]2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.[CH2:33](N(CC)CC)C.C(N)CC>C(Cl)Cl>[CH2:12]([NH:8][C:1]([NH:3][O:29][C@H:26]1[CH2:27][CH2:28][N:24]([S:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:32])([F:31])[F:13])[CH:16]=2)(=[O:23])=[O:22])[CH2:25]1)=[O:2])[CH2:11][CH3:33]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 67118437HCID 67118437, compound

Product 1

HCID 58235432HCID 58235432, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (162 mg, 1.00 mmol) was added to a solution of (S)—O-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yl)hydroxyl amine (155 mg, 0.50 mmol) and triethylamine (101 mg, 1.00 mmol) in CH2Cl2 (15 ml) and stirred at room temperature for 24 hours. Propan-1-amine (35.0 mg, 0.60 mmol) was added to the reaction mixture and stirred at room temperature for another 17 hours. The reaction mixture was washed with aqueous 0.1 N HCl solution (15 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: 50/50) to give (S)-1-propyl-3-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yloxy)urea (120 mg, 61%) as pale yellow oil: LCMS: 396 [M+1]+. 1H NMR (DMSO-d6) δ: 0.76-0.81 (3H, t), 1.34-1.41 (2H, m), 1.77-1.83 (1H, m), 2.01-2.06 (1H, m), 2.90-2.97 (2H, m), 3.16-3.28 (3H, m), 3.50-3.54 (1H, d), 4.22 (1H, s), 6.64-6.68 (1H, t), 7.83-7.89 (1H, t), 8.01 (1H, s), 8.07-8.13 (1H, t), 8.92 (1H, s).

Workup

  1. stirringstirred at room temperature for another 17 hours
  2. washThe reaction mixture was washed with aqueous 0.1 N HCl solution (15 ml), H2O (20 ml×3) and brine (20 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (ethyl acetate/petroleum ether: 50/50)

Sources & evidence

ORD record
ord-b93d9981cbf7427daf0fb29bc2614fd7
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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