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

HRID 1522527Notes

Reaction equation

HRID 1522527 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([OH:20])=O)[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:21][CH2:22][C:23]1[C:24](=[O:33])[NH:25][C:26]([CH3:32])=[CH:27][C:28]=1[CH2:29][CH2:30][CH3:31].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([NH:21][CH2:22][C:23]3[C:24](=[O:33])[NH:25][C:26]([CH3:32])=[CH:27][C:28]=3[CH2:29][CH2:30][CH3:31])=[O:20])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:15])([CH3:17])[CH3:16])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 398706041-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate

Product 1

HCID 715435666-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (53 mg, 0.194 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (71.3 mg, 0.242 mmol), 1-hydroxy-7-azabenzotriazole (52.8 mg, 0.388 mmol), EDC (74.3 mg, 0.388 mmol) and N-methylmorpholine (0.085 mL, 0.776 mmol) were suspended in Dimethyl Sulfoxide (DMSO) (10 mL) and stirred at room temperature for 16 hours. Added 25 mL of water and stirred for 10 minutes. The contents were filtered and dried, and collected as 70 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.33 Hz, 3 H), 0.96-1.09 (m, 4 H), 1.54 (m, J=7.52, 7.52, 7.52, 7.52, 7.33 Hz, 2 H), 1.68 (s, 9 H), 2.12 (s, 2 H), 2.17-2.27 (m, 1 H), 2.33 (s, 3 H), 2.5(2 H), 4.34 (d, J=5.05 Hz, 2 H), 5.89 (s, 1H), 7.01 (s, 1 H), 8.54 (t, J=4.80 Hz, 1 H), 11.50 (s, 1 H). LCMS(ES) [M+H]+ 436.1.

Workup

  1. stirringstirred for 10 minutes
  2. filtrationThe contents were filtered
  3. customdried
  4. customcollected as 70 mg

Sources & evidence

ORD record
ord-43c9310a165348c4835cf1f7bd690a59
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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