1,2-Dichloroethane → HCID 56598942, compound

HRID 476065Notes

Reaction equation

HRID 476065 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=O)[C:5]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=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>[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:18]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[N:7]=[C:2]([CH3:1])[CH:3]=1)=[O:20]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 16791219HCID 16791219, compound

Product 1

HCID 56598942HCID 56598942, 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-methyl-1-(phenylmethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (200 mg, 0.748 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (142 mg, 0.935 mmol), 1-hydroxy-7-azabenzotriazole (204 mg, 1.497 mmol), DMSO (10 mL), EDC (287 mg, 1.497 mmol), and N-methylmorpholine (0.329 mL, 2.99 mmol). The final product was collected as 0.25 g (83%). LCMS E-S (M+H)=402.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93-1.12 (m, 4H), 1.42 (d, J=6.82 Hz, 6H), 2.12 (s, 3H), 2.22 (s, 4H), 2.36 (s, 3H), 4.34 (d, J=4.80 Hz, 2H), 4.90-5.11 (m, 1H), 5.87 (s, 1H), 6.99 (s, 1H), 8.58 (s, 1H), 11.51 (s, 1H.

Workup

  1. customThe final product was collected as 0.25 g (83%)

Sources & evidence

ORD record
ord-08510bdac09e43778db1022621a77c71
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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