Trifluoromethanesulfonic acid → Biphenyl-1-carboxylic acid (R)-(6-(1-((2-pentoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide

HRID 2224740Notes

Reaction equation

HRID 2224740 reaction equation
OS(C(F)(F)F)(=O)=O.CS[CH:11]([N:13]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:14])[CH3:12].[NH2:23][C:24]1[CH:32]=[C:31]2[C:27]([CH2:28][C@@H:29]([OH:48])[C@@H:30]2[NH:33][C:34]([C:36]2[CH:41]=[CH:40][C:39](C3C=CC=CC=3)=[CH:38][CH:37]=2)=[O:35])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:18]([O:17][CH2:16][CH2:15][N:13]([CH3:14])[C:11](=[N:23][C:24]1[CH:32]=[C:31]2[C:27]([CH2:28][C@@H:29]([OH:48])[C@@H:30]2[NH:33][C:34]([C:36]2([C:24]3[CH:32]=[CH:31][CH:27]=[CH:26][CH:25]=3)[CH:37]=[CH:38][CH:39]=[CH:40][CH2:41]2)=[O:35])=[CH:26][CH:25]=1)[CH3:12])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 44185809(R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindaneHCID 86607039(1-Methylsulfanylethyl)(2-pentoxyethyl)methylamine

Product 1

HCID 86607038Biphenyl-1-carboxylic acid (R)-(6-(1-((2-pentoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amideYield 21.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve the crude triflic acid salt of (1-methylsulfanylethyl)(2-pentoxyethyl)methylamine (192.1 mg, 0.523 mmol) and biphenyl-4-carboxylic acid (R)-(6-amino-2(R)-hydroxyindan-1-yl)amide (170.8 mg, 0.496 mmol) in 10 mL pyridine and allow it to stir for 22 hours. Remove the solvent in vacuo and partition the residue between methylene chloride and saturated aqueous sodium hydrogen carbonate. Dry the organic layer with magnesium sulfate. Filter and remove the solvent in vacuo to give 112.3 mg of crude product. Purify via Biotage chromatography (10% MeOH/EtOAc 25% MeOH/EtOAc) to afford 27.8 mg of the titled product (11% yield). MS (ES): m/z 514.5 (M+H).

Workup

  1. customRemove the solvent in vacuo
  2. custompartition the residue between methylene chloride and saturated aqueous sodium hydrogen carbonate
  3. dry with materialDry the organic layer with magnesium sulfate
  4. filtrationFilter
  5. customremove the solvent in vacuo
  6. customto give 112.3 mg of crude product
  7. customPurify via Biotage chromatography (10% MeOH/EtOAc 25% MeOH/EtOAc)

Sources & evidence

ORD record
ord-703067d9053b49aa883ecd6bc44b6574
Source dataset
uspto-grants-2008_05
Patent number
US07378447B2

Reaction notes

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