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

HRID 475962Notes

Reaction equation

HRID 475962 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].FC(F)(F)C(O)=O.[NH2:29][CH2:30][C:31]1[C:32](=[O:44])[NH:33][C:34]([CH3:43])=[CH:35][C:36]=1[CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[CH:37]1([C:36]2[CH:35]=[C:34]([CH3:43])[NH:33][C:32](=[O:44])[C:31]=2[CH2:30][NH:29][C:13]([C:12]2[C:7]3[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=3[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=2)=[O:15])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 67124435HCID 67124435, compound

Product 1

HCID 56597703N-[(4-Cyclohexyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamideYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (169 mg, 0.6 mmol), 3-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone trifluoroacetate (221 mg, 0.660 mmol), EDC (150 mg, 0.780 mmol), HOAT (106 mg, 0.780 mmol), and N-methylmorpholine (0.264 mL, 2.400 mmol) in DMF (3 mL) were stirred at room temperature for 6 days. water (15 mL) was added to the slurry, and it was stirred for an hour. The precipitate was then collected by vacuum filtration and rinsed with EtOH (4 mL), and the solid was dried in the vacuum oven overnight to give the title compounds as an off-white solid (137 mg, 45%). LCMS E-S (M+H)=485.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.44 (m, 5H), 1.56 (d, J=6.57 Hz, 6H), 1.55-1.72 (m, 5H), 2.15 (s, 3H), 2.80-2.92 (m, 1H), 4.53 (d, J=4.55 Hz, 2H), 5.36 (spt, J=6.53 Hz, 1H), 6.03 (s, 1H), 8.18-8.23 (m, 2H), 8.26 (s, 1H), 8.45 (s, 1H), 8.75-8.82 (m, 2H), 9.01 (t, J=4.55 Hz, 1H), 11.59 (s, 1H).

Workup

  1. stirringwas stirred for an hour
  2. filtrationThe precipitate was then collected by vacuum filtration
  3. washrinsed with EtOH (4 mL)
  4. customthe solid was dried in the vacuum oven overnight

Sources & evidence

ORD record
ord-4d6a94fe679542bb8265f874849af74c
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

Loading…