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

HRID 1522492Notes

Reaction equation

HRID 1522492 reaction equation
[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[C:13]([C:14](O)=[O:15])[C:8]=2[C:7]([CH3:21])=[N:6]1)([CH3:4])[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=1[CH3:30].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:17]([CH3:20])([CH3:18])[CH3:19])[CH:12]=[C:13]([C:14]([NH:22][CH2:23][C:24]3[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=3[CH3:30])=[O:15])[C:8]=2[C:7]([CH3:21])=[N:6]1)([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 680786001,6-Bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 565992061,6-Bis(1,1-dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-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 1,6-bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.242 mmol), DMSO (2 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (68.5 mg, 0.363 mmol), N-methylmorpholine (0.106 mL, 0.968 mmol), 1-hydroxy-7-azabenzotriazole (65.9 mg, 0.484 mmol) and EDC (93 mg, 0.484 mmol). The final product was collected as 91 mg (87%). LCMS E-S (M+H)=424.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (s, 9 H), 1.74 (s, 9 H), 2.12 (s, 3 H), 2.23 (s, 3 H), 2.35 (s, 3 H), 4.35 (d, J=4.80 Hz, 2 H), 5.88 (s, 1 H), 7.15 (s, 1 H), 8.61 (t, J=4.93 Hz, 1 H), 11.52 (s, 1 H).

Workup

  1. customThe final product was collected as 91 mg (87%)

Sources & evidence

ORD record
ord-2c90a1b4915846a3ba8b91b7b0b3e00f
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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