Trifluoroacetic acid → HCID 178493571, compound

HRID 41769Notes

Reaction equation

HRID 41769 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH:14]([C:15]4[CH:20]=[CH:19][C:18]([CH:21]5[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]5)=[CH:17][CH:16]=4)[C:13](=[O:28])[CH2:12][C:11]3=[O:29])=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)(Cl)=O.[C:34](O)(C(F)(F)F)=O>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH:14]([C:15]4[CH:16]=[CH:17][C:18]([CH:21]5[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]5)=[CH:19][CH:20]=4)[C:13]([O:28][CH3:34])=[CH:12][C:11]3=[O:29])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24386Thionyl ChlorideHCID 178515848HCID 178515848, compound

Product 1

HCID 178493571HCID 178493571, compound

Procedure

The compound was synthesized starting from 1-(1H-benzo[d]imidazol-5-yl)-5-(4-(4-oxocyclohexyl)phenyl)pyrrolidine-2,4-dione (1.5 g, 3.87 mmol) and thionyl chloride (1.1 g, 9.1 mmol) according to method 6 described above. The compound was further treated with TFA (5 ml) at room temperature for 1 h. The volatiles were evaporated and the residue was partitioned between sodium bicarbonate solution and MeOH/CHCl3 (5/95). The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography to give the title compound.

Workup

  1. customThe compound was synthesized
  2. customThe volatiles were evaporated
  3. customthe residue was partitioned between sodium bicarbonate solution and MeOH/CHCl3 (5/95)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-54e93a156bda4084bf6d52b0eed88b98
Source dataset
uspto-grants-2013_09
Patent number
US08530670B2

Reaction notes

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