4-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one → (2-{4-(4-Fluoro-3-trifluoromethyl-phenyl)-2-[1-(6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-imidazol-1-yl}-ethyl)-methyl-carbamic acid benzyl ester

HRID 1685183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685183
Cl.Cl.[CH2:3]([O:10][C:11](=[O:38])[N:12]([CH2:14][CH2:15][N:16]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)[N:18]=[C:17]1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:40]1[C:41]2[CH2:48][C:47](=[O:49])[NH:46][C:42]=2[N:43]=[CH:44][N:45]=1>CN(C=O)C>[CH2:3]([O:10][C:11](=[O:38])[N:12]([CH2:14][CH2:15][N:16]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)[N:18]=[C:17]1[CH:32]1[CH2:33][CH2:34][N:35]([C:40]2[C:41]3[CH2:48][C:47](=[O:49])[NH:46][C:42]=3[N:43]=[CH:44][N:45]=2)[CH2:36][CH2:37]1)[CH3:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 86641608{2-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethyl}-methyl-carbamic acid benzyl ester dihydrochloride

Produkt 1

HCID 67264871(2-{4-(4-Fluoro-3-trifluoromethyl-phenyl)-2-[1-(6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-imidazol-1-yl}-ethyl)-methyl-carbamic acid benzyl esterAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine {2-[4-(4-fluoro-3-trifluoromethyl-phenyl)-2-piperidin-4-yl-imidazol-1-yl]-ethyl}-methyl-carbamic acid benzyl ester dihydrochloride (277 μmol; 160 mg); 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (1.30 equiv; 360 μmol; 61.1 mg); DMF (3 mL); TEA (7 equiv; 1.94 mmol; 270 μL) and heat to 160° C. in microwave for 45 min. Evaporate, dissolve the residue in DCM, wash with saturated sodium bicarbonate and evaporate the organic layer. Purify the residue on 40 g silica gel with 3% MeOH/DCM to provide the title compound (138.2 mg; 0.22 mmol; 78%). MS (ES+): m/z=638 (M+H).

Aufarbeitung

  1. customEvaporate
  2. dissolutiondissolve the residue in DCM
  3. washwash with saturated sodium bicarbonate
  4. customevaporate the organic layer
  5. customPurify the residue on 40 g silica gel with 3% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-ae470a45f6f2471fb17c131fddb0238b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148387B2

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