Diisopropylethylamine → HCID 86675140, compound

HRID 1504630Notes

Reaction equation

HRID 1504630 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].[Br:9][C:10]1[CH:24]=[C:23](/[CH:25]=[CH:26]/[CH:27]([C:32]2[CH:37]=[C:36]([Cl:38])[C:35]([Cl:39])=[C:34]([Cl:40])[CH:33]=2)[C:28]([F:31])([F:30])[F:29])[CH:22]=[CH:21][C:11]=1[C:12]([NH:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:13].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:9][C:10]1[CH:24]=[C:23](/[CH:25]=[CH:26]/[CH:27]([C:32]2[CH:33]=[C:34]([Cl:40])[C:35]([Cl:39])=[C:36]([Cl:38])[CH:37]=2)[C:28]([F:31])([F:29])[F:30])[CH:22]=[CH:21][C:11]=1[C:12]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])[CH2:17][CH2:16]1)=[O:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 27779723,3,3-Trifluoropropionic acidHCID 86675137HCID 86675137, compound

Product 1

HCID 86675140HCID 86675140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,3,3-trifluoropropanoic acid (0.02 g, 0.16 mmol) in CH2Cl2 (10.0 mL), (E)-2-bromo-N-(piperidin-4-yl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamide (0.1 g, 0.16 mmol), PYBOP (0.09 g, 0.17 mmol), and DIPEA (0.06 g, 0.48 mmol) were added at ambient temperature. The reaction mixture was stirred at ambient temperature for 5 h. The reaction mixture was diluted with CH2Cl2. The combined CH2Cl2 layer was washed with 3N HCl and saturated NaHCO3 solution, the separated CH2Cl2 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude compound. The crude compound was purified by column chromatography (SiO2, 100-200 mesh; eluting with 2% MeOH in CH2Cl2) to afford the title compound as an off white gummy material (0.035 g, 29. %).

Workup

  1. washThe combined CH2Cl2 layer was washed with 3N HCl and saturated NaHCO3 solution
  2. dry with materialthe separated CH2Cl2 layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude compound
  5. customThe crude compound was purified by column chromatography (SiO2, 100-200 mesh; eluting with 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a72bab9879b646d0a2f0f38f18d15ccd
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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