Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-butyl-1-pyridin-4-yl-1H-pyrazol-5-amine

HRID 1918105Notes

Reaction equation

HRID 1918105 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][NH:6][C:5](=O)[CH:4]=1)[NH2:2].[CH3:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[CH2:13][C:14]#[N:15]>>[NH2:15][C:14]1[N:1]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[N:2]=[C:12]([C:11]([CH3:18])([CH3:17])[CH3:10])[CH:13]=1

Participants

3

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 136108294-Hydrazinylpyridin-2(1H)-one

Product 1

HCID 109000523-tert-butyl-1-pyridin-4-yl-1H-pyrazol-5-amineYield 33%

Procedure

Following the procedure for Example 282A Step 1, 4-hydrazinylpyridin-2(1H)-one was heated at 80° C. overnight with 4,4-dimethyl-3-oxopentanenitrile. The reaction mixture was concentrated, triturated with DCM, and purified using silica gel chromatography eluting with a MeOH/DCM gradient (2-10%) to afford 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)pyridin-2(1H-one (307 mg, 33% yield). 1H NMR (300 MHz, DMSO d6) δ 1.18 (s, 9H), 5.43 (s, 1H), 5.47 (s, 2H), 6.55 (s, 1H), 6.66 (m, 1H), 7.37 (d, 1H), 11.40 (s, 1H); LC-MS (ESI) m/z 233 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with DCM
  3. custompurified
  4. washeluting with a MeOH/DCM gradient (2-10%)

Sources & evidence

ORD record
ord-3910ff27591a42f7b21c3d440e6bfa62
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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