Triethylsilane → HCID 89963456, compound

HRID 337969Notes

Reaction equation

HRID 337969 reaction equation
[F:1][C:2]1([F:45])[CH2:7][C@H:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18](CC3C=CC(OC)=CC=3OC)[C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)(=[O:17])=[O:16])=[C:11]([F:36])[CH:10]=2)[C@@H:5]([C:37]2[CH:38]=[N:39][N:40](COC)[CH:41]=2)[CH2:4][CH2:3]1.C([SiH](CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[F:45][C:2]1([F:1])[CH2:7][C@H:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)(=[O:16])=[O:17])=[C:11]([F:36])[CH:10]=2)[C@@H:5]([C:37]2[CH:41]=[N:40][NH:39][CH:38]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 89963460HCID 89963460, compound

Product 1

HCID 89963456HCID 89963456, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the 4-({(1S*,2R*)-5,5-difluoro-2-[1-(methoxymethyl)-1H-pyrazol-4-yl]cyclohexyl}oxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(pyrimidin-4-yl)benzenesulfonamide (0.12 g, 0.19 mmol) prepared in Example 147d and triethylsilane (0.15 mL) in dichloromethane (4.0 mL), trifluoroacetic acid (3.0 mL) was added at room temperature, and the reaction solution was stirred for 2 hours. The reaction solution was concentrated, then ethanol (1.0 mL) and 2 M hydrochloric acid (4.0 mL) were added to the residue, and the mixture was stirred at 100° C. for 3 hours. After allowing to cool, the reaction solution was neutralized with sodium hydrogencarbonate, and the resulting solid was collected by filtration. The solid thus collected by filtration was purified with silica gel chromatography (dichloromethane/methanol=95:5) to yield the title compound (40 mg, 48%) as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionethanol (1.0 mL) and 2 M hydrochloric acid (4.0 mL) were added to the residue
  3. stirringthe mixture was stirred at 100° C. for 3 hours
  4. temperatureto cool
  5. filtrationthe resulting solid was collected by filtration
  6. filtrationThe solid thus collected by filtration
  7. customwas purified with silica gel chromatography (dichloromethane/methanol=95:5)

Sources & evidence

ORD record
ord-e7b4a9fff44f491584b3e445bee035c6
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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