Triethylamine → HCID 57647087, compound

HRID 1171157Notes

Reaction equation

HRID 1171157 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:17]1=[O:27].[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(N(CC)CC)C>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][N:24]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:23][CH2:22]2)[C:17]1=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86629122HCID 86629122, compound

Product 1

HCID 57647087HCID 57647087, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (R)-3-(3,5-Dichloro-4′-fluoro-biphenyl-4-ylmethyl)-1-piperidin-4-yl-pyrrolidin-2-one trifluoroacetic acid (Preparation 29) (0.10 g, 0.19 mmol) in CH2Cl2 (3 mL) with methanesulfonyl chloride (0.02 mL, 0.28 mmol) and triethylamine (0.07 mL, 0.48 mmol) and stir the reaction for 1 hr at room temperature. Quench the reaction with 1N HCl and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 0.07 g (73%) of product. MS (m/e): 500 (M+1).

Workup

  1. customthe reaction for 1 hr at room temperature
  2. customQuench
  3. customthe reaction with 1N HCl
  4. extractionextract with Et2O
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-3f36692b78b6413f98a61eaa6902a96f
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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