Pyridine → methyl 4-{[(4-chlorobutyl)sulfonyl]amino}-1H-benzimidazole-6-carboxylate

HRID 852620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852620
[NH2:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.N1C=CC=CC=1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][S:26]([NH:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1)(=[O:28])=[O:27]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 742124-Chlorobutane-1-sulphonyl chlorideHCID 1419109Methyl 4-amino-1H-benzo[d]imidazole-6-carboxylate

Produkt 1

HCID 69360119methyl 4-{[(4-chlorobutyl)sulfonyl]amino}-1H-benzimidazole-6-carboxylateAusbeute 50,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-amino-1H-benzimidazole-6-carboxylate (D251) (1.1 g, 5.76 mmol, 1 equiv) in CH2Cl2 (80 ml) at room temperature were added pyridine (1.02 ml, 12.67 mmol, 2.2 equiv), 4-chloro-1-butanesulfonyl chloride (D20) (2.31 g, 12.1 mmol, 2.1 equiv) and DMAP (704 mg, 5.76 mmol, 1 equiv) and the resulting mixture was stirred for 1 h then concentrated in vacuo. The residue was diluted with AcOEt and the organic phase was washed with a 2N aqueous HCl solution and brine, then dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 2/3) gave methyl 4-{[(4-chlorobutyl)sulfonyl]amino}-1H-benzimidazole-6-carboxylate (D252) (1 g, 50%) as a colorless oil. [M+H]+=346.1, RT=2.97 min.

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted with AcOEt
  3. washthe organic phase was washed with a 2N aqueous HCl solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 2/3)

Quellen und Nachweise

ORD-Eintrag
ord-0651501f81d84b9d8d5bdc15981d3999
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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