1,2-Dichloroethane → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522515Notes

Reaction equation

HRID 1522515 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:19][CH2:20][C:21]1[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27].CN1CCOCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CS(C)=O>[CH3:27][C:26]1[CH:25]=[C:24]([CH3:28])[NH:23][C:22](=[O:29])[C:21]=1[CH2:20][NH:19][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]([CH2:16][CH2:17][CH3:18])[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 609838421-(1-Methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 56599210N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

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-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.283 mmol), DMSO(3 mL), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (80 mg, 0.425 mmol), N-methylmorpholine (0.124 mL, 1.132 mmol), 1-hydroxy-7-azabenzotriazole (77 mg, 0.566 mmol), and EDC (109 mg, 0.566 mmol). The collected solid was washed with water and methanol and dried under high vacuum to give 73 mg (68%) of product. LCMS E-S (M+H)=382.3 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82-1.10 (m, 3 H), 1.48 (d, J=6.8 Hz, 6 H), 1.77 (m, 2 H), 2.13 (s, 3 H), 2.21 (s, 3 H), 2.85 (t, J=7.6 Hz, 2 H), 4.36 (d, J=4.8 Hz, 2 H), 5.20 (m, 1 H), 5.90 (s, 1 H), 7.38-7.58 (m, 1 H), 8.26 (s, 1 H), 8.73 (t, J=4.7 Hz, 1 H), 11.57 (br. s., 1 H).

Workup

  1. washThe collected solid was washed with water and methanol
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-f3b1bcc45f614a7781d36bc226f9f5cd
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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