Triethylsilane → HCID 59614400, compound

HRID 409454Notes

Reaction equation

HRID 409454 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH2:6][N:7]([C:28]1[N:33]=[CH:32][C:31]([C:34]2[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=2)=[CH:30][N:29]=1)[C@@H:8]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH:23](O)[CH3:24])[C@H:10]([CH2:26][CH3:27])[CH2:9]1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O.ClCCCl>[F:45][C:43]([F:44])([F:46])[C:41]1[CH:40]=[C:5]([CH:4]=[C:3]([C:2]([F:48])([F:47])[F:1])[CH:42]=1)[CH2:6][N:7]([C@H:8]1[CH2:9][C@@H:10]([CH2:26][CH3:27])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:14]=2[CH2:23][CH3:24])[CH2:12]1)[C:28]1[N:29]=[CH:30][C:31]([C:34]2[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=2)=[CH:32][N:33]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 86648395HCID 86648395, compound

Product 1

HCID 59614400HCID 59614400, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-[2-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-trifluoromethyl-phenyl]-ethanol (29 mg, 0.04 mmol) in TFA (1 mL) and DCE (1 mL) is added triethylsilane (1 mL, 6.3 mmol) The reaction mixture is stirred at 80° C. for 4 hours. After removal of solvent and triethylsilane, the mixture is washed with brine and extracted with EtOAc. The combined organic layer is dried over MgSO4 then concentrated under reduced pressure to give (3,5-bis-trifluoromethyl-benzyl)-[(3S,5R)-5-ethyl-1-(2-ethyl-4-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine as a colorless oil (2 mg, 7%) after purification by silica gel column chromatography (eluent: n-hexane/EtOAc);

Workup

  1. customAfter removal of solvent and triethylsilane
  2. washthe mixture is washed with brine
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layer is dried over MgSO4
  5. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-969afcf355ff4a028ba4b220c3d81203
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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