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

HRID 476067Notes

Reaction equation

HRID 476067 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]([OH:18])=O)[C:7]3[CH:12]=[N:11][N:10]([CH2:13][CH2:14][CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[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.C(Cl)CCl.CN1CCOCC1>CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]([NH:19][CH2:20][C:21]3[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=3[CH3:27])=[O:18])[C:7]3[CH:12]=[N:11][N:10]([CH2:13][CH2:14][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 196165146-cyclopropyl-1-propyl-1H-pyrazolo(3,4-b)pyridine-4-carboxylic acid

Product 1

HCID 565989436-Cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-propyl-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-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (90 mg, 0.368 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (70 mg, 0.460 mmol), 1-hydroxy-7-azabenzotriazole (100 mg, 0.736 mmol), DMSO (10 mL), EDC (141 mg, 0.736 mmol), and N-methylmorpholine (0.162 mL, 1.472 mmol). The final product was collected as 0.118 g (84%). LCMS E-S (M+H)=380.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.78 (t, 3H), 0.99-1.16 (m, 4H), 1.85 (d, J=7.33 Hz, 2H), 2.13 (s, 3H), 2.22 (s, 4H), 4.25-4.43 (m, 4H), 5.90 (s, 1H), 7.43 (s, 1H), 8.21 (s, 1H), 8.75 (s, 1H), 11.57 (s, 1H).

Workup

  1. customThe final product was collected as 0.118 g (84%)

Sources & evidence

ORD record
ord-de5b80ed264a4d4ca8f26db7e4e13ce4
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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