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

HRID 476071Notes

Reaction equation

HRID 476071 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([CH:18]4[CH2:20][CH2:19]4)[CH:13]=[C:14]([C:15]([OH:17])=O)[C:9]=3[C:8]([CH3:21])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:22][CH2:23][C:24]1[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=1[CH3:30].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([CH:18]4[CH2:19][CH2:20]4)[CH:13]=[C:14]([C:15]([NH:22][CH2:23][C:24]4[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=4[CH3:30])=[O:17])[C:9]=3[C:8]([CH3:21])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 671241831-Cyclopentyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680785921-Cyclopentyl-6-cyclopropyl-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 1-cyclopentyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (160 mg, 0.561 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (119 mg, 0.785 mmol), 1-hydroxy-7-azabenzotriazole (153 mg, 1.121 mmol), EDC (215 mg, 1.121 mmol), N-methylmorpholine (0.247 mL, 2.243 mmol) and DMSO (10 mL). The final product was collected as 0.205 g (87%). LCMS E-S (M+H)=420.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03 (d, J=6.06 Hz, 4H), 1.85 (dd, J=9.35, 5.05 Hz, 3H), 2.12 (s, 4H), 2.16-2.28 (m, 6H), 2.30-2.44 (m, 7H), 2.63 (d, J=19.96 Hz, 3H), 4.34 (d, J=4.29 Hz, 2H), 5.31 (t, J=8.34 Hz, 1H), 5.87 (s, 1H), 7.01 (s, 1H), 8.59 (br. s., 1H), 11.52 (br. s., 1H).

Workup

  1. customThe final product was collected as 0.205 g (87%)

Sources & evidence

ORD record
ord-d900055a4d804989950a65aa1c2e119f
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

Loading…