Hydrogen iodide → HCID 58689455, compound

HRID 2224741Notes

Reaction equation

HRID 2224741 reaction equation
I.[CH3:2][N:3]([CH2:8][CH2:9][S:10][CH3:11])[CH:4](SC)[CH3:5].[NH2:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][C@@H:18]([OH:39])[C@@H:19]2[NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])=[CH:27][C:26]=2[F:38])=[O:24])=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH3:11][S:10][CH2:9][CH2:8][N:3]([CH3:2])[C:4](=[N:12][C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][C@@H:18]([OH:39])[C@@H:19]2[NH:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])=[CH:27][C:26]=2[F:38])=[O:24])=[CH:15][CH:14]=1)[CH3:5]

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 86607040HCID 86607040, compoundHCID 86607041HCID 86607041, compound

Product 1

HCID 58689455HCID 58689455, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

Dissolve the crude HI salt of methyl-(2-methylsulfanylethyl)(1-methylsulfanylethyl)amine (90.1 mg, 0.295 mmol) and 3,2′-difluorobiphenyl-4-carboxylic acid (R)-(6-amino-2(R)-hydroxyindan-1-yl)amide (101.3 mg, 0.266 mmol) in 10 mL pyridine. Allow the reaction to stir at 25° C. for 21 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 91.5 mg of crude product. Purify via silica gel column chromatography (2% MeOH/CHCl3 to 5% MeOH/CHCl3) to afford 30.5 mg of the titled product (22% yield). MS (ES): m/z 510.1(M+H).

Workup

  1. customthe reaction
  2. customRemove the solvent in vacuo
  3. custompartition the residue between methylene chloride and saturated aqueous sodium hydrogen carbonate
  4. dry with materialDry the organic layer with magnesium sulfate
  5. filtrationFilter
  6. customremove the solvent in vacuo
  7. customto give 91.5 mg of crude product
  8. customPurify via silica gel column chromatography (2% MeOH/CHCl3 to 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-9670d349af094844abe5b1e9eb04552d
Source dataset
uspto-grants-2008_05
Patent number
US07378447B2

Reaction notes

Loading…