Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-[2-(1-Carbamoylethylcarbamoyl)quinolin-6-yl]-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl Ester

HRID 1788458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788458
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]=[C:26]([C:31]([OH:33])=O)[CH:25]=[CH:24]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:34][C@H:35]([C:37]([NH2:39])=[O:38])[CH3:36].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:19]([O:18][C:16]([C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]=[C:26]([C:31](=[O:33])[NH:34][CH:35]([C:37](=[O:38])[NH2:39])[CH3:36])[CH:25]=[CH:24]4)=[N:9][C:10]=2[CH:15]=1)=[O:17])[CH3:20]

Komponenten

8

Edukt 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 81531DiisopropylethylamineHCID 444939L-AlaninamideHCID 2733179PyBroPHCID 576029956-(1-Cyclohexyl-5-ethoxycarbonyl-1H-benzimidazol-2-yl)quinoline-2-carboxylic Acid

Produkt 1

HCID 689195572-[2-(1-Carbamoylethylcarbamoyl)quinolin-6-yl]-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl EsterAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 100 mg (0.23 mmol) of Compound 402a, 86 mg (0.69 mmol) of L-alaninamide, 322 mg (0.69 mmol) of PyBroP, 84 mg (0.69 mmol) DMAP and 89 mg (0.69 mmol) DIEA in 5 mL anhydrous CH2Cl2 was stirred at room temperature for 24 h. To this solution was added 214 mg (0.92 mmol) of CSA. The solution was stirred for another 24 h, diluted with 10 mL CH2Cl2 and washed with 10 mL H2O. The solvent was dried and evaporated. The residue was chromatographed on silica gel using first hexane/EtOAc then CH2Cl2/MeOH as eluent yielding 50 mg yellow oil. MS: 514.28 (M+H+).

Aufarbeitung

  1. washwashed with 10 mL H2O
  2. customThe solvent was dried
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using first hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-ef9a621588f5428ca617a34cf18decac
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511145B2

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