Sodium hydride → 4-{6-Bromo-3-[(morpholin-4-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine

HRID 1398573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398573
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[N:23]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[O:12])=[N:7][N:8]2[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[N:23]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2233322-Amino-4-chloropyrimidineHCID 681818546-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole

Produkt 1

HCID 681816314-{6-Bromo-3-[(morpholin-4-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole (78%, 458 mg, 1.15 mmol) in DMF (8 mL) was added NaH (60% oil suspension, 73.71 mg, 1.84 mmol) at 0° C. Mixture was stirred at RT for 10 minutes before addition of 4-chloropyrimidin-2-amine (298.44 mg, 2.3 mmol). The mixture was stirred at RT for 10 minutes and then at 65° C. for 5 hr. Reaction mixture was quenched by addition of water (5 mL) and a little EtOAc (2 mL) was added. Precipitate formed was collected and dried under vacuum to give the title compound: 1H NMR (500 MHz, DMSO) delta 3.58-3.80 (6H, m), 3.87-4.13 (2H, m), 7.07 (1H, d, J=5.52 Hz), 7.59 (1H, dd, J=8.51, 1.42 Hz), 7.94 (1H, d, J=8.83 Hz), 8.35 (1H, d, J=5.52 Hz), 9.19 (1H, d, J=1.26 Hz); LC-MS: m/z=+404.8 (M+H)+.

Aufarbeitung

  1. waitat 65° C. for 5 hr
  2. customReaction mixture
  3. customwas quenched by addition of water (5 mL)
  4. additiona little EtOAc (2 mL) was added
  5. customPrecipitate formed
  6. customwas collected
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1e775331d92b492dbdce4524be8ba4ad
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

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