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

HRID 1522467Notes

Reaction equation

HRID 1522467 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][CH2:17][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:14]1([N:10]2[C:8]3[N:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[CH:5]=[C:6]([C:20]([NH:23][CH2:24][C:25]4[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=4[CH3:31])=[O:21])[C:7]=3[C:12]([CH3:13])=[N:11]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 671244651-cyclohexyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680792091-Cyclohexyl-6-cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-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-1-(1-cyclohexyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.501 mmol), and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (123 mg, 0.651 mmol). The product was collected as a solid, 0.190 g (87%). LCMS E-S (M+H)=434.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.07 (m, 4 H), 1.15-1.31 (m, 1 H), 1.36-1.52 (m, 2 H), 1.68 (br. s., 1 H), 1.77-1.99 (m, 6 H), 2.11 (s, 3 H), 2.18-2.29 (m, 4 H), 2.35 (s, 3 H), 4.33 (d, J=4.80 Hz, 2 H), 4.53-4.73 (m, 1 H), 5.87 (s, 1 H), 6.96 (s, 1 H), 8.58 (t, J=4.93 Hz, 1 H), 11.51 (s, 1 H).

Workup

  1. customThe product was collected as a solid, 0.190 g (87%)

Sources & evidence

ORD record
ord-85954950eef44a6d8b07f031ccfdf3e4
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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