Hydrofluoric Acid → HCID 178523815, compound

HRID 1690594Notes

Reaction equation

HRID 1690594 reaction equation
F.C([Si](C)(C)[O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:40])[N:16]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=2)[C:17]2[N:18]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[N:19]=[C:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH2:10][CH2:9]1)(C)(C)C>C(OC(C)=O)(C)C.[Cl-].[Na+].O.C(Cl)Cl>[Cl:39][C:35]1[CH:34]=[C:33]([N:16]([C:17]2[N:18]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[N:19]=[C:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[C:15]([NH:14][C@H:11]2[CH2:10][CH2:9][C@H:8]([OH:7])[CH2:13][CH2:12]2)=[O:40])[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 178455367HCID 178455367, compound

Product 1

HCID 178523815HCID 178523815, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 131729614iPrOAc brineSolvent

Procedure

Hydrofluoric acid (48%, 200 μl, 16 μmol) was added to a solution of trans-3-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-1-(3-chloro-phenyl)-1-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-urea (10 mg, 16 μmol) in CH3CN/CH2Cl2 1/1 (400 μl). The reaction mixture was stirred for 4 h at ambient temperature, diluted with CH2Cl2 (5 ml) and washed with saturated aqueous NaHCO3 solution and brine. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound (2 mg, 4 μmol; 25%) as brown solid. MS: m/e=495.5 [M+H+].

Workup

  1. washwashed with saturated aqueous NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f98419bd2304450e8c3d8ae65fdaf8f7
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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