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 475962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475962
[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

Komponenten

8

Edukt 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, Verbindung

Produkt 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-carboxamideAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4d6a94fe679542bb8265f874849af74c
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637509B2

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