Trifluoroacetic acid → HCID 23114615, compound

HRID 748860Notes

Reaction equation

HRID 748860 reaction equation
[Cl:1][C:2]1[C:3]([CH:21]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:4][C:5]([N:8]([CH2:10][CH2:11][N:12](C)[C:13](=O)OC(C)(C)C)[CH3:9])=[N:6][CH:7]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH:21]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:4][C:5]([N:8]([CH3:9])[CH2:10][CH2:11][NH:12][CH3:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 59750733HCID 59750733, compound

Product 1

HCID 23114615HCID 23114615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (2.0 ml) was dissolved tert-butyl 2-[N-[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridine-2-yl]-N-methylamino]ethyl-methylcarbamate (61 mg, 0.10 mmol), followed by the addition of anisole (40 μl) and trifluoroacetic acid (200 μl) at room temperature. The resulting mixture was stirred for 1 hour. The residue obtained by concentrating the reaction mixture under reduced pressure was purified by silica gel chromatography (3% methanol/chloroform→3% methanol, 3% tertbutylamine/chloroform), whereby the title compound (21 mg, 41%) was obtained as an oil.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customwas purified by silica gel chromatography (3% methanol/chloroform→3% methanol, 3% tertbutylamine/chloroform), whereby the title compound (21 mg, 41%)
  4. customwas obtained as an oil

Sources & evidence

ORD record
ord-eb660b9e5eec4f6997aed2099852d4e0
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…