Formaldehyde → HCID 10390073, Verbindung

HRID 2181411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181411
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH:14]=2)=[CH:4][CH:3]=1.[CH2:34]=O.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH:14]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 21354520HCID 21354520, Verbindung

Produkt 1

HCID 10390073HCID 10390073, VerbindungAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-(4-Fluorophenyl)-2-(4-piperidinyl)-5-(2-(1-(S)-phenylethyl)amino-4-pyridinyl)thiazole (500 mg 1.09 mmol) is dissolved in MeOH (11 ml) and treated with an aqueous 36%-solution of formaldehyde (0.17 ml 2.18 mmol) and NaBH4 (83 mg 2.18 mmol), which is added as a solid in 3 portions. After 30 min at room temperature the reaction mixture is poured on water and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4, filtered, evaporated to dryness and purified by SiO2 chromatography (tert.butyl methyl ether/MeOH/NH3conc. 95/4.5/0.5) to yield the title compound (550 mg 86%) as pale yellow foam.

Aufarbeitung

  1. additionis added as a solid in 3 portions
  2. additionAfter 30 min at room temperature the reaction mixture is poured on water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. custompurified by SiO2 chromatography (tert.butyl methyl ether/MeOH/NH3conc. 95/4.5/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-c1f5f4aa1cb5495b81ca34351c568861
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06891039B2

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