Triethylamine → HCID 178444600, compound

HRID 1807118Notes

Reaction equation

HRID 1807118 reaction equation
FC(F)(F)[C:3]([OH:5])=O.[Cl:8][C:9]1[C:10]([F:45])=[C:11]([C@@H:15]2[C@:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:18]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:17][C@H:16]2[C:35]([NH:37][C@H:38]2[CH2:43][CH2:42][C@H:41]([NH2:44])[CH2:40][CH2:39]2)=[O:36])[CH:12]=[CH:13][CH:14]=1.C([N:48](CC)CC)C>O1CCOCC1>[Cl:8][C:9]1[C:10]([F:45])=[C:11]([C@@H:15]2[C@:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:18]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:17][C@H:16]2[C:35]([NH:37][C@H:38]2[CH2:43][CH2:42][C@H:41]([NH:44][C:3]([NH2:48])=[O:5])[CH2:40][CH2:39]2)=[O:36])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178444599HCID 178444599, compound

Product 1

HCID 178444600HCID 178444600, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of rac-4-{[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-trans-cyclohexylamine trifluoroacetic acid salt (100 mg, 0.126 mmol) in 1,4-dioxane (5 mL), N-trimethylsilyl isocyanate (Aldrich, 42 uL, 0.316 mmol) was added followed by the addition of triethylamine (44 uL, 0.316 mmol). The mixture was stirred at rt overnight. The reaction was quenched with addition of water. The mixture was extracted with methylene chloride (2×10 mL) and the extracts were dried with magnesium sulfate. The solvent was removed and the residue was purified on a reverse phase HPLC to give a white solid. 39 mg.

Workup

  1. customThe reaction was quenched with addition of water
  2. extractionThe mixture was extracted with methylene chloride (2×10 mL)
  3. dry with materialthe extracts were dried with magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified on a reverse phase HPLC
  6. customto give a white solid

Sources & evidence

ORD record
ord-183db22393c3459790fb04c5443a1f37
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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