Trifluoroacetic acid → 5-(4,4-Difluorooctahydro-4aH-cyclopropa[3,4]cyclopenta[1,2-c]pyrrol-4a-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 629902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629902
[CH3:1][C:2]([CH3:34])([CH3:33])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]34[C:28]([F:30])([F:29])[CH:14]3[CH:15]3[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH:16]3[CH2:27]4)=[CH:10][CH:11]=2)[N:6]([CH3:31])[C:5]1=[O:32].FC(F)(F)C(O)=O>ClCCl>[F:30][C:28]1([F:29])[C:13]2([C:9]3[N:8]=[C:7]4[N:6]([CH3:31])[C:5](=[O:32])[N:4]([CH2:3][C:2]([CH3:34])([CH3:1])[CH3:33])[C:12]4=[CH:11][CH:10]=3)[CH2:27][CH:16]3[CH:15]([CH:14]12)[CH2:19][NH:18][CH2:17]3

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71136671tert-butyl 4a-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]-4,4-difluorooctahydro-2H-cyclopropa[3,4]cyclopenta[1,2-c]pyrrole-2-carboxylate

Produkt 1

HCID 711366875-(4,4-Difluorooctahydro-4aH-cyclopropa[3,4]cyclopenta[1,2-c]pyrrol-4a-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-butyl 4a-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]-4,4-difluorooctahydro-2H-cyclopropa[3,4]cyclopenta[1,2-c]pyrrole-2-carboxylate (30-2, 100 mg, 0.21 mmol) was added to a mixture of dichloromethane (2.0 mL) and trifluoroacetic acid (0.5 mL) at room temperature. After stirring for 18 h, the solvent was removed in vacuo. The resulting residue was then diluted with ethyl acetate (100 mL) and washed sequentially with saturated sodium bicarbonate (2×50 mL), water (1×50 mL) and brine (1×50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to give 1-[(2,2-Difluorocyclopropyl)methyl]-5-(1,2,3,3a,4,6a-hexahydrocyclopenta-[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (30-3) as a white solid. This material was carried on without further purification.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. additionThe resulting residue was then diluted with ethyl acetate (100 mL)
  3. washwashed sequentially with saturated sodium bicarbonate (2×50 mL), water (1×50 mL) and brine (1×50 mL)
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0d936da22ca3479b999eb478d0b678c8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315518B2

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