1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522489Notes

Reaction equation

HRID 1522489 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11](O)=[O:12])=[CH:8][C:7]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:6][C:5]=2[N:4]([CH:20]([CH3:22])[CH3:21])[N:3]=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].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:31][C:30]1[CH:29]=[C:28]([CH3:32])[NH:27][C:26](=[O:33])[C:25]=1[CH2:24][NH:23][C:11]([C:9]1[C:10]2[C:2]([CH3:1])=[N:3][N:4]([CH:20]([CH3:22])[CH3:21])[C:5]=2[N:6]=[C:7]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)[CH:8]=1)=[O:12]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 671244223-Methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 68079187N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in the same manner as described in example 109 using 3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (20 mg, 0.067 mmol), DMSO(1 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (19.10 mg, 0.101 mmol), N-methylmorpholine (0.030 mL, 0.270 mmol), 1-hydroxy-7-azabenzotriazole (18.37 mg, 0.135 mmol) and EDC (25.9 mg, 0.135 mmol). The final product was collected as 29 mg (100%). LCMS E-S (M+H)=431.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (d, J=6.57 Hz, 6 H), 2.12 (s, 3 H), 2.25 (s, 3 H), 2.46 (s, 3 H), 4.40 (d, J=5.0 Hz, 2 H), 5.29 (quin, J=6.7 Hz, 1 H), 5.89 (s, 1 H), 7.83 (s, 1 H), 8.19 (d, J=6.1 Hz, 2 H), 8.64-8.89 (m, 3 H), 11.55 (br. s., 1 H).

Workup

  1. customThe final product was collected as 29 mg (100%)

Sources & evidence

ORD record
ord-aa4ee9f05eca4c5f80554ce9f421ee7f
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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