1,2-Dichloroethane → HCID 56599076, compound

HRID 476073Notes

Reaction equation

HRID 476073 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:20](O)=[O:21])[C:7]3[C:12](C)=[N:11][N:10]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:23][CH2:24][C:25]1[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=1[CH3:31].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:20]([NH:23][CH2:24][C:25]3[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=3[CH3:31])=[O:21])[C:7]3[CH:12]=[N:11][N:10]([C:14]4[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=4)[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 67124654HCID 67124654, compound

Product 1

HCID 56599076HCID 56599076, compound

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-3-methyl-1-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (89 mg, 0.302 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (69.0 mg, 0.454 mmol), 1-hydroxy-7-azabenzotriazole (82 mg, 0.605 mmol), DMSO (20 mL), EDC (116 mg, 0.605 mmol), and N-methylmorpholine (0.133 mL, 1.210 mmol). The final product was collected as 0.110 g (80%). LCMS E-S (M+H)=429.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (br. s., 4H), 2.13 (br. s., 3H), 2.25 (br. s., 4H), 3.34 (br. s., 3H), 4.37 (br. s., 2H), 5.89 (br. s., 1H), 7.30 (br. s., 1H), 8.33 (br. s., 2H), 8.67 (br. s., 3H), 11.54 (br. s., 1H).

Workup

  1. customThe final product was collected as 0.110 g (80%)

Sources & evidence

ORD record
ord-8e1a297f99004dbc982b19358165cbc3
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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