Sodium hydride → HCID 71534334, Verbindung

HRID 1755430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755430
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:22])=[N:18][C:19]=1[O:20][CH3:21].[H-].[Na+]>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([NH:22][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[C:19]([O:20][CH3:21])[N:18]=2)[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 467391485,6-Dimethoxypyridin-2-amineHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Produkt 1

HCID 71534334HCID 71534334, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (2 g, 8.6 mmol) and 5,6-dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0° C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystallized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (2.4 g, 7.85 mmol, 91.2%) as light brown needles. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 8.26 (br. s., 1H) 7.95 (s, 1H) 7.81 (s, 1H) 7.55 (s, 1H) 7.15 (d, J=7.93 Hz, 1H) 6.58 (d, J=8.31 Hz, 1H) 4.12 (s, 3H) 3.89 (s, 3H); LC/MS: 305.9 [MH]+.

Aufarbeitung

  1. temperaturethen warmed to room temperature
  2. customAfter 15 h the reaction was quenched with saturated sodium bicarbonate solution
  3. additiondiluted with water and EtOAc
  4. filtrationAn insoluble solid was filtered off
  5. customThe filtrate was separated
  6. washthe aqueous phase was washed with EtOAc
  7. concentrationThe combined organic extracts were concentrated in vacuo
  8. customthe residue obtained
  9. customwas crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-6fd3233990ea48598cf851fcd2356294
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169259B2

Notizen zur Reaktion

Wird geladen…