Dimethylformamide → HCID 178486788, Verbindung

HRID 1012151

Reaktionsgleichung

Reaktionsgleichung von HRID 1012151
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]([OH:17])=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:29][O:30][C:31]1[C:45]([O:46][CH3:47])=[CH:44][C:34]2[NH:35][C:36]([C:38]3[C:42]([NH2:43])=[CH:41][NH:40][N:39]=3)=[N:37][C:33]=2[CH:32]=1.C(N(C(C)C)CC)(C)C>C1COCC1.CO>[CH3:47][O:46][C:45]1[C:31]([O:30][CH3:29])=[CH:32][C:33]2[NH:37][C:36]([C:38]3[C:42]([NH:43][C:15]([CH:11]4[O:12][CH2:13][CH2:14][N:9]([CH2:2][C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:10]4)=[O:17])=[CH:41][NH:40][N:39]=3)=[N:35][C:34]=2[CH:44]=1

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochlorideHCID 178486794HCID 178486794, Verbindung

Produkt 1

HCID 178486788HCID 178486788, VerbindungAusbeute 10,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of rac-4-benzyl-2-morpholinecarboxylic acid hydrochloride (77 mg, 0.30 mmol) in THF (2 ml) was added DMF (2.0 μl, 0.025 mmol) followed by oxalyl chloride (36 ul, 0.41 mmol). After stirring at room temperature for 20 min. the mixture was evaporated to dryness and then re-suspended in THF (2 ml). A solution of 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (60 mg, 0.2 mmol) and diisopropylethylamine (110 μl, 0.9 mmol) in THF (1 ml) was then added and the reaction stirred for at room temperature for 1 h. After 1 h, MeOH (1 ml) was added, the mixture concentrated and the residue purified through preparative LC/MS to give N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-rac-4-benzyl-2-morpholinecarboxamide (AT8769) as a white solid (10 mg, 9%). (LC/MS (basic method): Rt 2.86 min, [M+H]+ 463).

Aufarbeitung

  1. customwas evaporated to dryness
  2. stirringthe reaction stirred for at room temperature for 1 h
  3. waitAfter 1 h
  4. concentrationthe mixture concentrated
  5. customthe residue purified through preparative LC/MS

Quellen und Nachweise

ORD-Eintrag
ord-61ef1b4438d5482c8fa343a52267a128
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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