Methanol → HCID 89963570, compound

HRID 337744Notes

Reaction equation

HRID 337744 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:36]1[CH:41]=[CH:40][N:39]=[CH:38][N:37]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[C:24]2[N:28](C3CCCCO3)[N:27]=[CH:26][CH:25]=2)=[CH:12][C:11]=1[F:35])(=[O:9])=[O:8].C([SiH](CC)CC)C.CO>ClCCl.FC(F)(F)C(O)=O>[F:35][C:11]1[CH:12]=[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[C:24]2[NH:28][N:27]=[CH:26][CH:25]=2)[C:14]([F:16])=[CH:15][C:10]=1[S:7]([NH:6][C:36]1[CH:41]=[CH:40][N:39]=[CH:38][N:37]=1)(=[O:8])=[O:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 12052TriethylsilaneHCID 89963733HCID 89963733, compound

Product 1

HCID 89963570HCID 89963570, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(pyrimidin-4-yl)-4-({(1S*,2R*)-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]cyclohexyl}oxy)benzenesulfonamide (366 mg, 0.547 mmol) prepared in Example 22b and triethylsilane (0.40 mL) in dichloromethane (4.0 mL), trifluoroacetic acid (4.0 mL) was added at room temperature, and the reaction solution was stirred for 1 hour. To the reaction solution, methanol (4.0 mL) was added, and the mixture was further stirred at room temperature for 1 hour. The reaction solution was concentrated, and the residue was purified with silica gel chromatography (dichloromethane/methanol=95:5) to yield the title compound (182 mg, 61%) as a colorless solid.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hour
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=95:5)

Sources & evidence

ORD record
ord-b19a6c70113240e49ca29a575d28e9af
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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