Reaktion #598838

Reaktionsgleichung

3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanoic acid

N,N-Diisopropylethylamine

4-tert-butylbenzene-1,2-diamine

→

amide

Ausbeute 81.0%

N-(2-amino-4-(tert-butyl)phenyl)-3-(3-((((3 aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanamide

Ausbeute 81.0%

Lösungsmittel

N,N-Dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenpartially concentrated to ca. 2 mls
2. 2
   workup.ADDITIONNaHCO3 (saturated) added
3. 3
   ExtraktionThem mixture was extracted with EtOAc 3×
4. 4
   Trocknenthe combined organics were dried with MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by flash chromatography (DCM/7N NH3 in MeOH 95:5)

Vorschrift

N,N,N′,N′-Tetramethyl-0-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (1.52 g, 4.01 mmol) added to a solution of 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isobutyl)amino)cyclobutyl)propanoic acid (1.7 g, 2.7 mmol) and N,N-Diisopropylethylamine (1.54 ml, 8.82 mmol) and 4-tert-butylbenzene-1,2-diamine (0.527 g, 3.21 mmol) in N,N-Dimethylformamide (16.6 ml). The reaction was stirred overnight at RT, partially concentrated to ca. 2 mls and then NaHCO3 (saturated) added. Them mixture was extracted with EtOAc 3× and the combined organics were dried with MgSO4 filtered, concentrated and purified by flash chromatography (DCM/7N NH3 in MeOH 95:5) to yield the desired amide (1.71 g) as a solid.

Quelle