1,2-Dichloroethane → N-[(5-Fluoro-4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 475967Notes

Reaction equation

HRID 475967 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](O)=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:3].Cl.[NH2:23][CH2:24][C:25]1[C:26](=[O:34])[NH:27][C:28]([CH3:33])=[C:29]([F:32])[C:30]=1[CH3:31].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[F:32][C:29]1[C:30]([CH3:31])=[C:25]([CH2:24][NH:23][C:13]([C:12]2[C:7]3[CH:6]=[N:5][N:4]([CH:2]([CH3:3])[CH3:1])[C:8]=3[N:9]=[C:10]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)[CH:11]=2)=[O:14])[C:26](=[O:34])[NH:27][C:28]=1[CH3:33]

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 712810993-(aminomethyl)-5-fluoro-4,6-dimethyl-2(1H)-pyridinone hydrochloride

Product 1

HCID 56597705N-[(5-Fluoro-4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

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, 0.60 mmol), 3-(aminomethyl)-5-fluoro-4,6-dimethyl-2(1H)-pyridinone hydrochloride (136 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) was stirred at room temperature for 3 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 compound as 220 mg (76%). LCMS E-S (M+H)=435.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (d, 7H), 2.18 (d, J=2.78 Hz, 3H), 2.25 (d, J=2.02 Hz, 3H), 4.45 (d, J=4.80 Hz, 2H), 5.37 (spt, J=6.65 Hz, 1H), 8.19-8.25 (m, 2H), 8.29 (s, 1H), 8.44 (s, 1H), 8.74-8.81 (m, 2H), 9.07 (t, J=4.80 Hz, 1H), 11.66 (br. 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-92debe0ceeba4c94819fec15380df322
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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