Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 67271642, compound

HRID 1696506Notes

Reaction equation

HRID 1696506 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][NH2:12])[CH:9]=2)[CH:4]=[N:3]1.[CH3:13][C:14]([CH3:21])([CH3:20])[C:15](=O)[CH2:16][C:17]#[N:18]>CCO>[C:14]([C:15]1[CH:16]=[C:17]([NH2:18])[N:11]([C:8]2[CH:9]=[C:10]3[C:5]([CH:4]=[N:3][NH:2]3)=[CH:6][CH:7]=2)[N:12]=1)([CH3:21])([CH3:20])[CH3:13]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67272092HCID 67272092, compound

Product 1

HCID 67271642HCID 67271642, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1H-indazol-6-yl)-hydrazine hydrochloride and 4,4-dimethyl-3-oxo-pentanenitrile (17 g, 1.05 eq) in EtOH (200 mL) was heated at reflux overnight. The reaction was concentrated and the residue purified by column chromatography to yield 3-t-butyl-1-(1H-indazol-6-yl)-1H-pyrazol-5-amine (21 g, 58% yield, for two steps). 1H NMR (300 MHz, DMSO-d6): 8.21 (s, 1H), 7.96 (d, J=8.1 Hz, 1H), 7.81 (s, 1H), 7.25 (d, J=8.1 Hz, 1H), 5.71 (s, 1H), 1.31 (s, 9H); MS (ESI) m/z: 256 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-a41b9e23f3d1405ab92bfceb78ee4e2c
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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