Hydrazine → HCID 70982737, compound

HRID 1479186Notes

Reaction equation

HRID 1479186 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:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:15]=2)[C:10]([N:25]2C(=O)C3C(=CC=CC=3)C2=O)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN.C(Cl)Cl.CC(C)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[CH:15]=2)[C:10]([NH2:25])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 9321Hydrazine2×HCID 21584124Propan-2-one--dichloromethane (1/1)HCID 70982230HCID 70982230, compound

Product 1

HCID 70982737HCID 70982737, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-indazole-1-carboxylic acid tert-butyl ester (1.17 g, 2.37 mmol) in dry THF (20 ml), under argon atmosphere, was treated with 3.56 ml of 1M hydrazine in THF (3.56 mmol). The mixture was stirred at reflux for 1 h then more 1M hydrazine in THF was added (8 ml). After stirring for additional 2 h at reflux, the reaction mixture was cooled to r.t. and the precipitated solid filtered and washed with THF. The filtrate was evaporated to dryness and the residue purified by flash chromatography over silica gel eluting with DCM/acetone 7:3 affording 785 mg (yield: 91%) of the title compound as a yellowish solid.

Workup

  1. temperatureat reflux for 1 h
  2. stirringAfter stirring for additional 2 h
  3. temperatureat reflux
  4. filtrationthe precipitated solid filtered
  5. washwashed with THF
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-98b1ca9be27e46cfb3499671af657343
Source dataset
uspto-grants-2016_08
Patent number
US09408850B2

Reaction notes

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