4-Cyclopropyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile → 3-(Aminomethyl)-4-cyclopropyl-6-methyl-2(1H)-pyridinone

HRID 593837Notes

Reaction equation

HRID 593837 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[O:16])[NH:5][C:6]([CH3:15])=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13]CCC1.C1(C2C=C(C)NC(=O)C=2C#N)CC1>>[NH2:1][CH2:2][C:3]1[C:4](=[O:16])[NH:5][C:6]([CH3:15])=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 671240524-Cyclopropyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrileHCID 671243593-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone2×

Product 1

HCID 671242083-(Aminomethyl)-4-cyclopropyl-6-methyl-2(1H)-pyridinone

Procedure

The title compound was prepared in the same manner as described for 3-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone (Intermediate 3) using 4-cyclopropyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (5 g, 28.7 mmol). Obtained: 0.50 g (10%). LCMS E-S (M+H)=179.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.76-11.78 (br s, 1H), 7.82-7.92 (br s, 3H), 5.61 (s, 1H), 3.94-3.99 (m, 2H), 2.11 (s, 3H), 1.98-2.05 (m, 1H), 0.95-1.01 (m, 2H), 0.74-0.79 (m, 2H).

Workup

  1. customObtained

Sources & evidence

ORD record
ord-c450d89730e2495b9795ed53f62e0db8
Source dataset
uspto-grants-2016_01
Patent number
US09242962B2

Reaction notes

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