Methyl iodide → HCID 66607308, compound

HRID 1810254Notes

Reaction equation

HRID 1810254 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]([C:35](=[O:37])[CH3:36])[C@@H:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][C@@H:26]2[OH:34])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.I[CH3:40].[H-].[Na+]>CN(C=O)C.Cl.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:38])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]([C:35](=[O:37])[CH3:36])[C@@H:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][C@@H:26]2[O:34][CH3:40])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66608575HCID 66608575, compound

Product 1

HCID 66607308HCID 66607308, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To (2′-{[acetyl-((1R,2S)-2-hydroxy-indan-1-yl)-amino]-methyl}-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.163 g, 0.31 mmol) and iodomethane (0.02 mL, 0.34 mmol) in DMF (1.6 mL) was added sodium hydride (60% in mineral oil; 0.015 g, 0.37 mmol), and the mixture was stirred at room temperature for 1 hour. Once minimal starting material was seen by analytical LCMS, the solution was diluted with aqueous 1N HCl and CH2Cl2. The organic layer was separated, dried over MgSO4., filtered, and concentrated to give the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtration, filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b35388e9296348a9bc6c29fbbc4bba61
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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