1,2-Dichloroethane → 1-Cyclobutyl-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 476070Notes

Reaction equation

HRID 476070 reaction equation
[CH:1]1([N:5]2[C:9]3[N:10]=[C:11]([CH:17]4[CH2:19][CH2:18]4)[CH:12]=[C:13]([C:14](O)=[O:15])[C:8]=3[C:7]([CH3:20])=[N:6]2)[CH2:4][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([N:5]2[C:9]3[N:10]=[C:11]([CH:17]4[CH2:18][CH2:19]4)[CH:12]=[C:13]([C:14]([NH:21][CH2:22][C:23]4[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=4[CH3:29])=[O:15])[C:8]=3[C:7]([CH3:20])=[N:6]2)[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 671243571-Cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680786551-Cyclobutyl-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-cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (164 mg, 0.604 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (129 mg, 0.846 mmol), 1-hydroxy-7-azabenzotriazole (165 mg, 1.209 mmol), EDC (232 mg, 1.209 mmol), N-methylmorpholine (0.266 mL, 2.418 mmol), and DMSO (10 mL). The final product was collected as 0.240 g (98%). LCMS E-S (M+H)=406.3. 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 0.240 g (98%)

Sources & evidence

ORD record
ord-e8476c88016544bdbb7c96656333759f
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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