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

HRID 1522458Notes

Reaction equation

HRID 1522458 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:15]([OH:17])=O)[C:7]3[CH:12]=[N:11][N:10]([CH2:13][CH3:14])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:18][CH2:19][C:20]1[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:15]([NH:18][CH2:19][C:20]3[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])=[O:17])[C:7]3[CH:12]=[N:11][N:10]([CH2:13][CH3:14])[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 167927676-cyclopropyl-1-ethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680784076-Cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-ethyl-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-ethyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (91 mg, 0.394 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (75 mg, 0.493 mmol), 1-hydroxy-7-azabenzotriazole (107 mg, 0.788 mmol), DMSO(10 mL), EDC (151 mg, 0.788 mmol), and N-methylmorpholine (0.173 mL, 1.577 mmol). The final product was collected as 0.090 g (63%). LCMS E-S (M+H)=366.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (d, J=6.32 Hz, 4 H), 1.39 (t, J=7.20 Hz, 3 H), 2.13 (s, 3 H), 2.19-2.32 (m, 4 H), 4.36 (d, J=4.80 Hz, 2 H), 4.42 (q, J=7.07 Hz, 2 H), 5.90 (s, 1 H), 7.43 (s, 1 H), 8.21 (s, 1 H), 8.75 (t, J=4.67 Hz, 1 H), 11.57 (br. s., 1 H).

Workup

  1. customThe final product was collected as 0.090 g (63%)

Sources & evidence

ORD record
ord-c1a68c3850b74fc484e122b612419406
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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