Water → {(R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

HRID 15992

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[C:17]1[N:22]=[C:21]2[N:23]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]4[O:34][CH2:33][CH2:32][C:31]=4[CH:35]=3)[N:24]=[N:25][C:20]2=[N:19][CH:18]=1.O>CN(C=O)C>[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:17]2[N:22]=[C:21]3[N:23]([CH2:26][C:27]4[CH:28]=[CH:29][C:30]5[O:34][CH2:33][CH2:32][C:31]=5[CH:35]=4)[N:24]=[N:25][C:20]3=[N:19][CH:18]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 23 °C

Versuchsvorschrift

To a solution of (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (37 mg, 0.165 mmoL) in anhydrous DMF (2 mL) was added NaH (60% in oil, 7 mg, 0.18 mmol). The solution was stirred at 23° C. for 15 minutes. 6-Bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (50 mg, 0.15 mmol) was added and the reaction solution was microwaved at 100° C. for 30 min. Water (10 mL) was added and the aqueous layer was extracted with EtOAc (3×10 mL). The combined extracts were dried with Na2SO4, and concentrated to provide {(R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (67 mg, 99% yield).

Aufarbeitung

customthe reaction solution was microwaved at 100° C. for 30 min
extractionthe aqueous layer was extracted with EtOAc (3×10 mL)
dry with materialThe combined extracts were dried with Na2SO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-1a07db2710054cb7abb34a1549b5204b
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732604B2

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