3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one → 6-Cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522469Notes

Reaction equation

HRID 1522469 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:20](O)=[O:21])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:23][CH2:24][C:25]1[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=1[CH3:31]>>[CH:1]1([C:4]2[CH:5]=[C:6]([C:20]([NH:23][CH2:24][C:25]3[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=3[CH3:31])=[O:21])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 680831046-Cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680791846-Cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Procedure

The title compound was prepared in the same manner as described in example 109 using 6-cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.498 mmol), and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (98 mg, 0.647 mmol). The product was collected as a solid, 0.170 g (78%). LCMS E-S (M+H)=436.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.14 (m, 4 H), 1.79 (dd, J=12.63, 2.27 Hz, 2 H), 2.05-2.18 (m, 5 H), 2.19-2.27 (m, 4 H), 2.36 (s, 3 H), 3.53 (t, J=11.12 Hz, 2 H), 3.98 (dd, J=11.49, 3.41 Hz, 2 H), 4.33 (d, J=4.80 Hz, 2 H), 4.87 (m, J=11.53, 11.53, 4.11, 3.92 Hz, 1 H), 5.87 (s, 1 H), 6.99 (s, 1 H), 8.59 (t, J=4.93 Hz, 1 H), 11.51 (s, 1 H).

Workup

  1. customThe product was collected as a solid, 0.170 g (78%)

Sources & evidence

ORD record
ord-142cbc0433304493b9af88ff2668049d
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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