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

HRID 475951Notes

Reaction equation

HRID 475951 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=1.Cl.[NH2:19][CH2:20][C:21]1[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([NH:19][CH2:20][C:21]2[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])=[O:17])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:13])[CH3:14])[C:6]=2[N:7]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 11430Potassium CarbonateHCID 181649HOAtHCID 438104513-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one hydrochlorideHCID 86677623HCID 86677623, compound

Product 1

HCID 565974266-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-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 17 using 6-chloro-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (486.6 mg, 1.92 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone HCl (489 mg, 2.59 mmol), 1-hydroxy-7-azabenzotriazole (392 mg, 2.88 mmol), N-methylmorpholine (0.84 ml, 7.67 mmol) and EDC (552 mg, 2.88 mmol). An additional 10 mL DMSO was added to the reaction mixture to facilitate stirring, and 10% K2CO3 was used instead of 50% aq. NaOH during the work up. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (d, 6H), 2.12 (s, 3H), 2.22 (s, 3H), 2.40 (s, 3H), 4.34 (d, J=5.05 Hz, 2H), 5.05 (quin, J=6.63 Hz, 1H), 5.88 (s, 1H), 7.16 (s, 1H), 8.78 (t, J=4.93 Hz, 1H), 11.53 (br. s., 1H).

Sources & evidence

ORD record
ord-ac2e6d21fffc4a5baa1f760d28449682
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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