Dimethylformamide → N-[[6-[1,6-dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]methyl]-cyclopropanecarboxamide

HRID 17102

Reaktionsgleichung

Reaktionsgleichung von HRID 17102
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10]C.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=N1.C([N:26]([CH:29](C)C)CC)(C)C.[CH:32]1([C:35]([OH:37])=O)[CH2:34][CH2:33]1.[C:38](O)([C:40](F)(F)F)=O.C[N:46](C)C=O>O.CO>[CH3:2][N:3]1[C:4]2=[C:38]3[CH:40]=[C:10]([C:18]4[N:14]=[C:22]([CH2:17][NH:16][C:35]([CH:32]5[CH2:34][CH2:33]5)=[O:37])[CH:21]=[CH:20][CH:19]=4)[NH:9][C:8]3=[N:7][C:6]([NH:26][CH3:29])=[C:5]2[N:46]=[CH:12]1

Komponenten

9

Edukt 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acid2×HCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 57393213N-[[6-[1,6-dihydro-1-methyl-4-(methylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-2-pyridinyl]methyl]-cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a mixture of A215 (0.020 g, 0.065 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.019 g, 0.098 mmol), 1-hydroxybenzotriazole (0.013 g, 0.098 mmol), and diisopropylethylamine (0.034 mL, 0.195 mmol) in anhydrous dimethylformamide (2 mL) was added cyclopropylcarboxylic acid (8.00 μL, 0.098 mmol). The reaction mixture was stirred at room temperature overnight. Concentration under pressure followed by purification by flash silica gel chromatography using a 5% mixture of methanol in dichloromethane afforded 0.012 g (50%) of A218 as a yellow solid. The compound had an HPLC retention time=1.99 min. (Column: Chromolith SpeedROD 4.6×50 mm—4 min.; Solvent A=10% MeOH, 90% H2O, and 0.1% TFA; Solvent B=90% MeOH, 10% H2O, and 0.1% TFA) and a LC/MS M+1=376.40.

Aufarbeitung

  1. concentrationConcentration under pressure
  2. customfollowed by purification by flash silica gel chromatography
  3. customafforded 0.012 g (50%) of A218 as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-eab24ac768e847f2b55ea80beb8050ec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737279B2

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