1,2-Dichloroethane → 1-(1,1-Dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522504Notes

Reaction equation

HRID 1522504 reaction equation
[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:12]=[C:13]([C:14]([OH:16])=O)[C:8]=2[C:7]([CH3:25])=[N:6]1)([CH3:4])[CH3:3].[NH2:26][CH2:27][C:28]1[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:4][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:12]=[C:13]([C:14]([NH:26][CH2:27][C:28]3[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=3[CH3:34])=[O:16])[C:8]=2[C:7]([CH3:25])=[N:6]1)([CH3:1])[CH3:3]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 680786021-(1,1-Dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680801341-(1,1-Dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(1,1-dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.206 mmol) in DMSO (1 mL) were added 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (19.10 mg, 0.101 mmol), N-methylmorpholine (0.030 mL, 0.270 mmol), 1-hydroxy-7-azabenzotriazole (18.37 mg, 0.135 mmol) and EDC (25.9 mg, 0.135 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with water (10 mL), stirred for 10 min., and filtered. The contents were dried under high vacuum and collected as 71 mg (71%). LCMS E-S (M+H)=474.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.79 (s, 9 H), 2.12 (s, 3 H), 2.25 (s, 3 H), 2.39 (s, 3 H), 3.33 (s, 1 H), 4.38 (d, J=4.80 Hz, 2 H), 5.88 (s, 1 H), 7.10 (d, J=8.84 Hz, 2 H), 7.61 (s, 1 H), 8.16 (d, J=8.84 Hz, 2 H), 8.70 (s, 1 H), 11.53 (s, 1 H).

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. stirringstirred for 10 min.
  3. filtrationfiltered
  4. customThe contents were dried under high vacuum
  5. customcollected as 71 mg (71%)

Sources & evidence

ORD record
ord-5932d8dcc99f4ff39568dfa21eab7e20
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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