Isopropylamine → 2-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethyl isopropylcarbamate

HRID 602682Notes

Reaction equation

HRID 602682 reaction equation
[C:1](=O)([O:32]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4](=[C:13]1[CH2:16][N:15]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:14]1)[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[CH:6]=1.[CH:43]([NH2:46])([CH3:45])[CH3:44]>C(Cl)Cl>[CH:43]([NH:46][C:1](=[O:32])[O:2][CH2:3][C:4](=[C:13]1[CH2:16][N:15]([CH:17]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:14]1)[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[CH:6]=1)([CH3:45])[CH3:44]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 113769992-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethyl 4-nitrophenyl carbonate

Product 1

HCID 114212272-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethyl isopropylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 45 mg (0.073 mmol) of 2-{1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-2-(3,5-difluorophenyl)ethyl 4-nitrophenyl carbonate in 3 mL of methylene chloride was added 0.3 mL of isopropylamine and stirred for 4 h at rt. The reaction mixture was then concentrated and the residue was purified by silica gel chromatography with hexanes/ethyl acetate=4:1 to afford the title compound as a white solid. 1NMR (CDCl3) δ 1.15 (d, 6H, J=5.7 Hz), 3.90 (br s, 1H), 3.99 (s, 2H), 4.06 (s, 2H), 4.54 (s, 1H), 4.74 (s, 2H), 6.68-6.74 (m, 3H), 7.29-7.39 (m, 8H); Mass Spectrum: m/e=531 (M+1 35Cl, 35Cl) and 533 (M+1 35Cl, 37Cl).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by silica gel chromatography with hexanes/ethyl acetate=4:1

Sources & evidence

ORD record
ord-940d06bd07ba4533aca20b34ea2fe6bc
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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