Trifluoroacetic acid → HCID 23114565, compound

HRID 2080428Notes

Reaction equation

HRID 2080428 reaction equation
[Cl:1][C:2]1[C:3]([CH:23]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15]C(=O)OC(C)(C)C)[CH2:9]2)=[N:6][CH:7]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:15][CH2:14][CH:10]1[O:11][CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[C:3]([CH:23]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)(=[O:33])=[O:34])[C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 59750874HCID 59750874, compound

Product 1

HCID 23114565HCID 23114565, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (1.5 ml) was dissolved t-butyl [4-[5-chloro-4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-2-yl]morpholin-2-yl]methylcarbamate (30 mg, 0.05 mmol). To the resulting solution were added anisole (30 μl) and trifluoroacetic acid (150 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% t-butylamine/chloroform) to give the title compound (17 mg, 67%) 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% t-butylamine/chloroform)

Sources & evidence

ORD record
ord-55585fb0b8d44464931e07e1003ee7e9
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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