1,2-Dichloroethane → 6-Cyclopropyl-1-(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 1522464Notes

Reaction equation

HRID 1522464 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:18](O)=[O:19])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:21][CH2:22][C:23]1[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=1[CH3:29].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([NH:21][CH2:22][C:23]3[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=3[CH3:29])=[O:19])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:16])([CH3:17])[CH3:15])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 398706041-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 565990756-Cyclopropyl-1-(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 for intermediate 56 using 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (210 mg, 0.768 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (158 mg, 1.037 mmol), 1-hydroxy-7-azabenzotriazole (209 mg, 1.537 mmol), EDC (295 mg, 1.537 mmol), N-methylmorpholine (0.338 mL, 3.07 mmol), and DMSO(10 mL). The final product was collected as 0.280 g (89%). LCMS E-S (M+H)=408.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02 (dddd, 4 H), 1.69 (m, 9 H), 2.12 (s, 3 H), 2.22 (m, 4 H), 2.33 (s, 3 H), 4.34 (d, J=4.80 Hz, 2 H), 5.87 (s, 1 H), 7.04 (s, 1 H), 8.55 (m, 1 H), 11.51 (s, 1 H).

Workup

  1. customThe final product was collected as 0.280 g (89%)

Sources & evidence

ORD record
ord-90542b56dbe84228bd8e98ed0445f9bb
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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