Tetrabutylammonium Fluoride → HCID 89962716, compound

HRID 338017Notes

Reaction equation

HRID 338017 reaction equation
[Si]([O:8][C@@H:9]1[CH2:14][C@H:13]([O:15][C:16]2[C:21]([Cl:22])=[CH:20][C:19]([S:23]([N:26]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=3[O:42][CH3:43])[C:27]3[CH:32]=[CH:31][N:30]=[CH:29][N:28]=3)(=[O:25])=[O:24])=[C:18]([F:44])[CH:17]=2)[C@@H:12]([C:45]2[N:49]([CH3:50])[N:48]=[CH:47][CH:46]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:22][C:21]1[C:16]([O:15][C@H:13]2[CH2:14][C@@H:9]([OH:8])[CH2:10][CH2:11][C@@H:12]2[C:45]2[N:49]([CH3:50])[N:48]=[CH:47][CH:46]=2)=[CH:17][C:18]([F:44])=[C:19]([S:23]([N:26]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=2[O:42][CH3:43])[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][N:28]=2)(=[O:25])=[O:24])[CH:20]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89963000HCID 89963000, compound

Product 1

HCID 89962716HCID 89962716, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 120c by using the 4-{[(1S*,2R*,5S*)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(pyrimidin-4-yl)benzenesulfonamide (174 mg, 0.233 mmol) prepared in Example 163g, tetrabutyl ammonium fluoride (1.0 M solution in THF; 0.466 mL, 0.466 mmol) and THF (5.0 mL), to yield the title compound (148 mg, 93%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-d90b106380584028976d1d9a8f6c0896
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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