Triethylamine → 4-[[(5-amino-4-oxo-1H-pyridin-2-yl)methylamino]methylidene]-6-iodoisoquinoline-1,3-dione

HRID 2236823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236823
[NH2:1][C:2]1[C:3]([OH:10])=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1.C(N(CC)CC)C.CO[CH:20]=[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([I:31])[CH:29]=2)[C:24](=[O:32])[NH:23][C:22]1=[O:33]>CN(C)C=O>[NH2:1][C:2]1[C:3]([OH:10])=[CH:4][C:5]([CH2:8][NH:9][CH:20]=[C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([I:31])[CH:29]=3)[C:24](=[O:32])[NH:23][C:22]2=[O:33])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 686910194-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dioneHCID 1785102595-Amino-2-aminomethyl-pyridin-4-ol

Produkt 1

HCID 1785080254-[[(5-amino-4-oxo-1H-pyridin-2-yl)methylamino]methylidene]-6-iodoisoquinoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-2-aminomethyl-pyridin-4-ol (60 mg, 0.19 mmole as the dihydrobromide), 3 mL of N,N-dimethylformamide and triethylamine (101 uL, 0.72 mmole) were stirred for 15 mins, 4-methoxymethylene-6-iodo-4H-isoquinoline-1,3-dione (63 mg, 0.19 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness, taken up in dimethylsulfoxide and purified by HPLC (acetonitrile-water with 0.2% trifluoroacetic acid). The product is isolated by evaporation in-vacuo to give a brown solid, 5.5 mg, (5%); MS (ES+): m/z 437.0 (M+H).

Aufarbeitung

  1. stirringthe reaction mixture stirred for one hour
  2. customThe reaction mixture is evaporated to dryness
  3. custompurified by HPLC (acetonitrile-water with 0.2% trifluoroacetic acid)
  4. customThe product is isolated by evaporation in-vacuo
  5. customto give a brown solid, 5.5 mg, (5%)

Quellen und Nachweise

ORD-Eintrag
ord-1eb632d4d7ce43f49177dc646dd70360
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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