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

HRID 475963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475963
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]([OH:18])=O)[C:7]3[CH:12]=[N:11][N:10]([CH:13]([CH3:15])[CH3:14])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[NH2:26][CH2:27][C:28]1[C:29](=[O:41])[NH:30][C:31]([CH3:40])=[CH:32][C:33]=1[CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CCO.CN(C=O)C>[CH:34]1([C:33]2[CH:32]=[C:31]([CH3:40])[NH:30][C:29](=[O:41])[C:28]=2[CH2:27][NH:26][C:16]([C:6]2[C:7]3[CH:12]=[N:11][N:10]([CH:13]([CH3:14])[CH3:15])[C:8]=3[N:9]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]=2)=[O:18])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 25259926-cyclopropyl-1-(propan-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 67124435HCID 67124435, Verbindung

Produkt 1

HCID 68078883N-[(4-Cyclohexyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The title compound was prepared in the same manner as described in example 15 from 6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (147 mg, 0.60 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), N-methylmorpholine (0.264 mL, 2.400 mmol) and DMF (3 mL), wherein the stir time was 3 d and the final product was not treated with EtOH. The final product was collected as 193 mg (68%). LCMS E-S (M+H)=448.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01-1.11 (m, 4H), 1.15-1.43 (m, 5H), 1.47 (d, J=6.57 Hz, 6H), 1.55-1.76 (m, 5H), 2.15 (s, 3H), 2.19-2.28 (m, 1H), 2.83 (t, J=11.12 Hz, 1H), 4.45 (d, J=5.05 Hz, 2H), 5.12 (spt, J=6.69 Hz, 1H), 6.02 (s, 1H), 7.37 (s, 1H), 8.21 (s, 1H), 8.74 (t, J=4.80 Hz, 1H), 11.56 (s, 1H).

Aufarbeitung

  1. customThe title compound was prepared in the same manner
  2. customThe final product was collected as 193 mg (68%)

Quellen und Nachweise

ORD-Eintrag
ord-98728306fce84179a89c412a6b9cc9f0
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637509B2

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