Hydrochloric Acid → 5-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)pyridin-2(1H)-one

HRID 871706Notes

Reaction equation

HRID 871706 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][NH:9][C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)C=CC=CC=1.[CH3:23][C:24]([CH3:31])([CH3:30])[C:25](=O)[CH2:26][C:27]#[N:28].Cl>>[NH2:28][C:27]1[N:9]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)[N:8]=[C:25]([C:24]([CH3:31])([CH3:30])[CH3:23])[CH:26]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 86653535HCID 86653535, compound

Product 1

HCID 222178465-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)pyridin-2(1H)-oneYield 6.1%

Procedure

5-(2-(Diphenylmethylene)hydrazinyl)pyridin-2(1H)-one (950 mg, 3.29 mmol) was treated with 4,4-dimethyl-3-oxopentanenitrile (620 mg, 4.93 mmol) and 6N HCl (2.70 mL, 16.4 mmol) according to the procedure in Example 303A Step 2. Purification by flash chromatography (silica, 1-8% MeOH/DCM) afforded 5-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)pyridin-2(1H)-one (46 mg, 0.20 mmol, 6%). 1H NMR (300 MHz, DMSO-d6) δ 11.65 (br s, 1H), 7.55-7.51 (m, 2H), 6.39 (d, 1H), 5.29 (s, 1H), 5.11 (s, 2H), 1.21 (s, 9H); LC-MS (ESI) m/z 233 (M+H)+.

Workup

  1. customPurification by flash chromatography (silica, 1-8% MeOH/DCM)

Sources & evidence

ORD record
ord-b975b15c3b4f474cb1d70e3d1e061022
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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