Water → HCID 136377221, compound

HRID 1479189Notes

Reaction equation

HRID 1479189 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C)C)[CH:15]=2)[C:10]([NH2:25])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O.C(Cl)Cl.CCOC(C)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([NH2:25])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 21226138Dichloromethane ethylacetateHCID 70982737HCID 70982737, compound

Product 1

HCID 136377221HCID 136377221, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-amino-6-(tert-butyl-dimethyl-silanyloxy)-indazole-1-carboxylic acid tert-butyl ester 672 mg (1.85 mmol) in dry THF (10 ml) was treated with 1M TBAF in THF (1.85 ml, 1.85 mmol) and stirred at r.t. for 30 min. Water (20 ml) was then added and the mixture extracted with EtOAc (3×50 ml). The separated organic layers were combined, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography over silica gel eluting with DCM/EtOAc 6:4 affording 429 mg (yield: 93%) of the title compound.

Workup

  1. extractionthe mixture extracted with EtOAc (3×50 ml)
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b2322bac74a449c095b8b3c4580e079e
Source dataset
uspto-grants-2016_08
Patent number
US09408850B2

Reaction notes

Loading…