Dimethylformamide → [4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methanol

HRID 73676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73676
CN(C=O)C.[NH2:6][C:7]1[C:12]2=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1.[Cl-].[CH2:19]=[N+:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CO>[NH2:6][C:7]1[C:12]2=[CH:13][C:14]([CH2:16][OH:17])=[C:15]([CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:11]2[N:10]=[CH:9][N:8]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 11367014Morpholinium, 4-methylene-, chlorideHCID 55297730HCID 55297730, Verbindung

Produkt 1

HCID 57955268[4-Amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of DMF (50 mL) was added (4-aminopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanol (550 mg, 3.35 mmol) and 4-methylenemorpholin-4-ium chloride (Eur. J. Med. Chem. 1989, 24, 379-384) (636 mg, 4.69 mmol). The solution was stirred at rt for 1 h and then the solvent was evaporated. The oil was triturated with CH2Cl2 and a white solid was collected. The free based was obtained by stirring over a Dowex 66 solid support resin in MeOH. The material was filtered and evaporated yielding 794 mg (90%) of the desired product as a white solid. MS [M+H]+=264; LCMS RT=1.07.

Aufarbeitung

  1. customthe solvent was evaporated
  2. customThe oil was triturated with CH2Cl2
  3. customa white solid was collected
  4. customThe free based was obtained
  5. filtrationThe material was filtered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d984b3b423f440aeb1181f2f44658f6e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829185B2

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