Diisopropylethylamine → 2-(1H-Benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

HRID 605868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605868
F[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1OCC[C@H]2N.Cl[C:14]1[N:19]=C(Cl)C([N+]([O-])=O)=C[N:15]=1.CCN(C(C)C)C(C)C.Cl[C:34]1[N:39]=[C:38]([NH:40][C@H:41]2[C:50]3[C:45](=[C:46]([F:51])[CH:47]=[CH:48][CH:49]=3)[O:44][CH2:43][CH2:42]2)[C:37]([N+:52]([O-:54])=[O:53])=[CH:36][N:35]=1>C1COCC1>[N:15]1([C:34]2[N:39]=[C:38]([NH:40][C@H:41]3[C:50]4[C:45](=[C:46]([F:51])[CH:47]=[CH:48][CH:49]=4)[O:44][CH2:43][CH2:42]3)[C:37]([N+:52]([O-:54])=[O:53])=[CH:36][N:35]=2)[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:11]=2[N:19]=[CH:14]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 46911919(R)-8-fluorochroman-4-amineHCID 59704905(R)-2-chloro-N-(8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

Produkt 1

HCID 597049352-(1H-Benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(R)-8-Fluorochroman-4-amine (60 mg) was added to a solution of 2,4-dichloro-5-nitropyrimidine (70 mg) and DIEA (0.14 mL) in THF (5 mL) at −78° C. The reaction mixture was stirred for a further 15 min at −78° C. then removed from the cold bath and allowed to warm to RT. A one molar solution of the sodium salt of benzimidazole (0.7 ml, stock solution prepared via the addition of sodium hydride to a benzimidazole solution in THF) was added to the reaction intermediate ((R)-2-chloro-N-(8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine) and the resulting mixture was stirred at RT overnight. Purification via column chromatography (elution with MeOH/DCM) gave the titled compound (120 mg), MH+=407.

Aufarbeitung

  1. customthen removed from the cold bath
  2. temperatureto warm to RT
  3. customA one molar solution of the sodium salt of benzimidazole (0.7 ml, stock solution prepared via the addition of sodium hydride to a benzimidazole solution in THF)
  4. stirringthe resulting mixture was stirred at RT overnight
  5. customPurification
  6. washvia column chromatography (elution with MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-ebdd6726f1c54ef0b61f0ec2bd91efa8
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915268B2

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