Dichloromethane → 3-Chloro-4-{2-[2-(6-chloro-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid

HRID 1161302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161302
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14](O)=[O:15])[C:11]3[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.C[O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([Cl:39])[CH:33]=1.C([O-])(O)=O.[Na+].ClCCl>S(Cl)(Cl)=O>[Cl:39][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][C:35]=1[NH:38][C:14](=[O:15])[CH:13]([N:12]1[C:11]2[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=2[N:9]=[C:8]1[C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C:31]([OH:40])=[O:30]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 1515284Methyl 4-Amino-3-chlorobenzoateHCID 86632022[2-(6-Chloro-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexylacetic acid

Produkt 1

HCID 441976913-Chloro-4-{2-[2-(6-chloro-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

The title compound was prepared by heating [2-(6-chloro-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexylacetic acid (200 mg, 0.46 mmol) in 5 ml thionylchloride to 80° C. for 4 h. The solvent was evaporated and the residue taken up in dichloromethane. 4-Amino-3-chloro-benzoic acid methyl ester (85 mg, 0.46 mmol) were added and the reaction mixture stirred at rt overnight. The crude product was worked up by addition of a solution of 1 M NaHCO3 and extraction of the aqueous layer with dichloromethane. Organic layers were combined, dried over MgSO4 and evaporated to dryness. The residue was taken up in methanol (3 ml) and 1N NaOH (1 ml) added. The mixture was stirred at rt overnight, the solvent evaporated and the product isolated via preparative HPLC. MS (ES+): 560 (M+H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. addition1N NaOH (1 ml) added
  5. stirringThe mixture was stirred at rt overnight
  6. customthe solvent evaporated
  7. customthe product isolated via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d9c84aa98f984483a388e061efb6dcc9
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816540B2

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