Triethylsilane → HCID 71711787, compound

HRID 337921Notes

Reaction equation

HRID 337921 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:31]1[CH:36]=[CH:35][N:34]=[CH:33][N:32]=1)[S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C@H:17]2[CH2:21][CH2:20][CH2:19][C@@H:18]2[C:22]2[N:26]([CH2:27][CH3:28])[N:25]=[CH:24][CH:23]=2)=[C:12]([F:29])[C:11]=1[F:30])(=[O:9])=[O:8].C([SiH](CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[CH2:27]([N:26]1[C:22]([C@H:18]2[CH2:19][CH2:20][CH2:21][C@@H:17]2[O:16][C:13]2[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][N:32]=3)(=[O:8])=[O:9])=[C:11]([F:30])[C:12]=2[F:29])=[CH:23][CH:24]=[N:25]1)[CH3:28]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 89962536HCID 89962536, compound

Product 1

HCID 71711787HCID 71711787, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To the N-(2,4-dimethoxybenzyl)-4-{[(1S,2R)-2-(1-ethyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-2,3-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (100.3 g, 167 mmol) prepared in Example 119b and triethylsilane (30 mL) in dichloromethane (300 mL), trifluoroacetic acid (300 mL) was added with cooling on ice, and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was concentrated, and the residue was purified with silica gel chromatography (ethyl acetate/methanol=9:1) to yield the title compound as a colorless solid. A suspension of this title compound in ethyl acetate (200 mL) was further irradiated with ultrasonic wave for 20 minutes. The suspension was filtered, and crystals collected by filtration were washed with ethyl acetate and dried at 40° C. for 24 hours to yield the title compound (32.9 g, 44%) as colorless crystals.

Workup

  1. temperaturewith cooling on ice
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified with silica gel chromatography (ethyl acetate/methanol=9:1)

Sources & evidence

ORD record
ord-562982c23c844f90b544de91c920c7f8
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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