Isopropylamine → HCID 70179502, compound

HRID 2227200Notes

Reaction equation

HRID 2227200 reaction equation
Br[C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH3:20])[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:4]=2[N:3]=1.[CH:26]([NH2:29])([CH3:28])[CH3:27].[OH-].[Na+].CCOC(C)=O.CCCCCC>C(O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:4]2[N:3]=[C:2]([NH:29][CH:26]([CH3:28])[CH3:27])[N:6]([C@@H:7]3[O:19][C@H:18]([CH3:20])[C@@H:13]([OH:14])[C@H:8]3[OH:9])[C:5]=2[CH:21]=1

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 70177980HCID 70177980, compound

Product 1

HCID 70179502HCID 70179502, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-6-chloro-1-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)-1H-benzimidazole and 10 mL of isopropylamine in 5 mL of absolute ethanol was refluxed for 18 h. To this resultant mixture was added 1 mL of 1N NaOH and the resultant solution was dry-packed in silica gel. Flash column chromatography on silica gel with EtOAc/hexane (1:1) gave 0.15 g of a still impure product. Further purification on a silica gel preparative plate using EtOAc/hexane (1:1) gave 0.06 g (28%) of the title compound as a foam. 1H NMR (DMSO-d6) δ1.18 (d, 6H, 2×CH3), 1.35 (d, 3H, CH3), 3.7-3.8 (m, 1H, CH), 3.8-3.9 (m, 1H, CH), 4 (sextet, 1H, CH), 4.3 (q, 1H, CH), 5.2-5.21 (m, 2H, 2×OH), 5.61 (d, 1H, CH), 6.38 (d, 1H, aromatic), 6.95 (d, 1H, aromatic), 7.1-7.2 (m, 2H, aromatic & NH).

Workup

  1. temperaturewas refluxed for 18 h
  2. customFurther purification on a silica gel preparative plate

Sources & evidence

ORD record
ord-037c1510eb854fe195e2e73c3d8106a3
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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