Water → HCID 136377220, compound

HRID 1479188Notes

Reaction equation

HRID 1479188 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]([NH:25][C:26](=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O.CCOCC>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]([NH:25][C:26](=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 70982171HCID 70982171, compound

Product 1

HCID 136377220HCID 136377220, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-(tert-butyl-dimethyl-silanyloxy)-3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-indazole-1-carboxylic acid tert-butyl ester 1.88 g (3.33 mmol) in dry THF (20 ml) was treated with 1M TBAF in THF (4 ml, 4 mmol) and stirred at r.t. for 30 min. Water (20 ml) was then added and the mixture extracted with EtOAc (100 ml). The separated organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography over silica gel eluting with DCM/MeOH/30% NH3 92:8:0.8 affording, after trituration with Et2O, 1.5 g (yield: 100%) of the title compound.

Workup

  1. extractionthe mixture extracted with EtOAc (100 ml)
  2. dry with materialThe separated organic layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography over silica gel eluting with DCM/MeOH/30% NH3 92:8:0.8 affording

Sources & evidence

ORD record
ord-ff5f5b5dcb1d4b5caea42e58b9f134cf
Source dataset
uspto-grants-2016_08
Patent number
US09408850B2

Reaction notes

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