Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 67272323, compound

HRID 1930325Notes

Reaction equation

HRID 1930325 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][NH2:12])=[CH:8][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:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[NH:2][N:3]=[CH:4]3)[N:12]=1)([CH3:21])([CH3:20])[CH3:13]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67271720(1H-Indazol-5-yl)-hydrazine hydrochloride

Product 1

HCID 67272323HCID 67272323, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1H-indazol-5-yl)-hydrazine hydrochloride and 4,4-dimethyl-3-oxo-pentanenitrile (19 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-5-yl)-1H-pyrazol-5-amine (23 g, 60% for two steps). 1H NMR (300 MHz, DMSO-d6): δ 8.24 (s, 1 H), 8.06 (s, 1 H), 7.75 (d, J=9.0 Hz, 1 H), 7.45 (dd, J=9.0 Hz, 1.8 Hz, 1 H), 5.7 (s, 1H), 1.31 (s, 9 H); 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-1942f37c0d4b4b44882afec12d08039c
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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