3,5-Bis(trifluoromethyl)phenyl isocyanate → Tert-butyl 4-[1-({[3,5-bis(trifluoromethyl)phenyl]amino}carbonyl)azetidin-3-yl]piperazine-1-carboxylate

HRID 1788350Notes

Reaction equation

HRID 1788350 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:2]1.[N:18]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)=[C:19]=[O:20]>O1CCCC1>[F:28][C:27]([F:29])([F:30])[C:25]1[CH:26]=[C:21]([NH:18][C:19]([N:1]2[CH2:4][CH:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[CH2:2]2)=[O:20])[CH:22]=[C:23]([C:31]([F:34])([F:32])[F:33])[CH:24]=1

Participants

4

Reactant 2

HCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanateHCID 21183794tert-Butyl 4-(azetidin-3-yl)piperazine-1-carboxylate

Product 1

HCID 23140263Tert-butyl 4-[1-({[3,5-bis(trifluoromethyl)phenyl]amino}carbonyl)azetidin-3-yl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 2 (986 mg) in tetrahydrofuran (12 mL) was dropwise added 1-isocyanato-3,5-bis(trifluoromethyl)benzene (0.85 mL), and the mixture was stirred for 30 minutes. The reaction solution was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give the compound of the present invention (1.413 g) having the following physical data.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)
  3. customto give the compound of the present invention (1.413 g)

Sources & evidence

ORD record
ord-4559a6888c6b47bd998d55458b50c4ed
Source dataset
uspto-grants-2009_03
Patent number
US07511159B2

Reaction notes

Loading…