1,2-Dichloroethane → HCID 68078594, compound

HRID 1522479Notes

Reaction equation

HRID 1522479 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=1[CH3:30].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:30][C:29]1[CH:28]=[C:27]([CH3:31])[NH:26][C:25](=[O:32])[C:24]=1[CH2:23][NH:22][C:13]([C:12]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=2[N:9]=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:11]=1)=[O:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 68078594HCID 68078594, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in the same manner as described in example 109 using 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (60 mg, 0.213 mmol), DMSO(2 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (60.1 mg, 0.319 mmol) HCl salt, N-methylmorpholine (0.093 mL, 0.850 mmol), 1-hydroxy-7-azabenzotriazole (57.9 mg, 0.425 mmol), and EDC (81 mg, 0.425 mmol). The final product was collected as 66 mg (74%). LCMS E-S (M+H)=446.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, J=6.0 Hz, 6 H), 2.13 (br. s., 3 H), 2.23 (br. s., 3 H), 4.43 (m, 2 H), 5.37 (m, 1 H), 5.91 (br. s., 1 H), 8.15-8.34 (m, 3 H), 8.44 (s, 1 H), 8.78 (br. s., 2 H), 9.00 (br. s., 1 H), 11.58 (br. s., 1 H).

Workup

  1. customThe final product was collected as 66 mg (74%)

Sources & evidence

ORD record
ord-0aa285d926924a2d88bdae76b5ed0bb2
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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