1,2-Dichloroethane → HCID 68078819, compound

HRID 1522508Notes

Reaction equation

HRID 1522508 reaction equation
[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:13]([C:14](O)=[O:15])[C:8]=2[C:7]([CH3:23])=[N:6]1)([CH3:4])[CH3:3].[NH2:24][CH2:25][C:26]1[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=1[CH3:32].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:3][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:13]([C:14]([NH:24][CH2:25][C:26]3[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=3[CH3:32])=[O:15])[C:8]=2[C:7]([CH3:23])=[N:6]1)([CH3:4])[CH3:1]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 67124417HCID 67124417, compound

Product 1

HCID 68078819HCID 68078819, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in the same manner as described in example 121 using 1-(1,1-dimethylethyl)-3-methyl-6-[3-pyridinyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (58 mg, 0.167 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (47 mg, 0.251 mmol), N-methylmorpholine (0.092 mL, 0.836 mmol), 1-hydroxy-7-azabenzotriazole (46 mg, 0.334 mmol), EDC (64 mg, 0.334 mmol), and DMSO (1 mL). The product was collected as 73 mg (96%). LCMS E-S (M+H)=445.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.81 (s, 9 H), 2.12 (s, 3 H), 2.25 (s, 3 H), 2.42 (s, 3 H), 4.39 (d, J=5.05 Hz, 2 H), 5.89 (s, 1 H), 7.59 (dd, J=8.08, 4.80 Hz, 1 H), 7.78 (s, 1 H), 8.55 (dt, J=8.15, 1.86 Hz, 1 H), 8.68 (dd, J=4.80, 1.52 Hz, 1 H), 8.74 (t, J=5.05 Hz, 1 H) 9.38 (d, J=1.77 Hz, 1 H), 11.54 (s,1 H).

Workup

  1. customThe product was collected as 73 mg (96%)

Sources & evidence

ORD record
ord-4edc5f6c7b214325a890da92ddd81cc6
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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