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

HRID 1522486Notes

Reaction equation

HRID 1522486 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:20]=[CH:19][S:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:21][CH2:22][C:23]1[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=1[CH3:29].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:29][C:28]1[CH:27]=[C:26]([CH3:30])[NH:25][C:24](=[O:31])[C:23]=1[CH2:22][NH:21][C:13]([C:12]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=2[N:9]=[C:10]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH:11]=1)=[O:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 671242341-(1-Methylethyl)-6-(3-thienyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 56599205N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(3-thienyl)-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-(1-methylethyl)-6-(3-thienyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.244 mmol), DMSO(2 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (68.9 mg, 0.365 mmol) HCl salt, N-methylmorpholine (0.107 mL, 0.974 mmol), 1-hydroxy-7-azabenzotriazole (33.2 mg, 0.244 mmol) and EDC (93 mg, 0.487 mmol). The final product was collected as 75 mg (73%). LCMS E-S (M+H)=422.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (d, J=6.8 Hz, 6 H), 2.13 (s, 3 H), 2.23 (s, 3 H), 4.41 (d, J=4.8 Hz, 2 H), 5.30 (quin, J=6.6 Hz, 1 H), 5.91 (s, 1 H), 7.71 (dd, J=5.0, 3.0 Hz, 1 H), 7.92 (d, J=5.0 Hz, 1 H), 8.09 (s, 1 H), 8.34 (s, 1 H), 8.37 (d, J=1.8 Hz, 1 H), 8.79-8.95 (m, 1 H), 11.58 (s, 1 H).

Workup

  1. customThe final product was collected as 75 mg (73%)

Sources & evidence

ORD record
ord-a88b426ef64444fca1744c8161e74900
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…