Triethylamine → HCID 24852107, compound

HRID 1171159Notes

Reaction equation

HRID 1171159 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][N:37]=[C:38]=[O:39].C(N(CC)CC)C>C(Cl)Cl>[CH3:36][NH:37][C:38]([N:24]1[CH2:25][CH2:26][CH:21]([N:18]2[CH2:19][CH2:20][C@@H:16]([CH2:15][C:14]3[C:13]([Cl:28])=[CH:12][C:11]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)=[CH:10][C:9]=3[Cl:8])[C:17]2=[O:27])[CH2:22][CH2:23]1)=[O:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 86629122HCID 86629122, compound

Product 1

HCID 24852107HCID 24852107, compoundYield 106.7%

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 methyl isocyanate (21 mg, 0.36 mmol) and triethylamine (0.07 mL, 0.48 mmol). Stir the reaction overnight at room temperature. Quench the reaction with 1N HCl and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Purify the crude by silica gel column chromatography using Hexanes:EtOAc to elute pure product. Remove the solvent to afford 0.097 g (84%) of product. MS (m/e): 478 (M+1).

Workup

  1. customthe reaction overnight 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. customPurify the crude by silica gel column chromatography
  9. washEtOAc to elute pure product
  10. customRemove the solvent

Sources & evidence

ORD record
ord-9023b3b097204c019745b0df97b27eb2
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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