Triethylsilane → HCID 71711784, compound

HRID 337934Notes

Reaction equation

HRID 337934 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][N:30]=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]([CH3:27])[N:25]=[CH:24][CH:23]=2)=[CH:12][C:11]=1[F:28])(=[O:9])=[O:8].C([SiH](CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[F:28][C:11]1[CH:12]=[C:13]([O:16][C@H:17]2[CH2:21][CH2:20][CH2:19][C@@H:18]2[C:22]2[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=2)[CH:14]=[CH:15][C:10]=1[S:7]([NH:6][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][N:30]=1)(=[O:8])=[O:9]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 89962132HCID 89962132, compound

Product 1

HCID 71711784HCID 71711784, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the N-(2,4-dimethoxybenzyl)-2-fluoro-4-{[(1S,2R)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (8.35 g, 14.7 mmol) prepared in Example 124b and triethylsilane (11.75 mL, 73.6 mmol) in dichloromethane (147 mL), trifluoroacetic acid (14.7 mL) was added at room temperature, and the reaction solution was stirred for 1 hour. The reaction solution was concentrated, and the residue was purified with silica gel chromatography (ethyl acetate) to yield the title compound as a colorless solid. A suspension of this title compound in a hexane/dichloromethane mixed solvent was further irradiated with ultrasonic wave for 1 hour. The suspension was filtered, and crystals collected by filtration were washed with hexane and dried at 40° C. for 24 hours to yield the title compound (5.95 g, 97%) as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified with silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9d38364199bc4914a3f2856f5d27a264
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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