1,2-Dichloroethane → HCID 56599076, compound

HRID 1522465Notes

Reaction equation

HRID 1522465 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., 4 H), 2.13 (br. s., 3H), 2.25 (br. s., 4 H), 3.34 (br. s., 3 H), 4.37 (br. s., 2 H), 5.89 (br. s., 1 H), 7.30 (br. s., 1 H), 8.33 (br. s., 2 H), 8.67 (br. s., 3 H), 11.54 (br. s., 1 H).

Workup

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

Sources & evidence

ORD record
ord-1a692cdf51c5414987a2c134c5471ec0
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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