Water → HCID 10274305, compound

HRID 1829801Notes

Reaction equation

HRID 1829801 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][C@H:26]([C@H:28]([N:36]1[CH:40]=[C:39]([C:41]([NH2:43])=[O:42])[N:38]=[CH:37]1)[CH2:29][CH2:30]OS(C)(=O)=O)[CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:25][C@H:26]([C@H:28]([N:36]1[CH:40]=[C:39]([C:41]([NH2:43])=[O:42])[N:38]=[CH:37]1)[CH2:29][CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 111649271-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide

Product 1

HCID 10274305HCID 10274305, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under N2, to a solution of 6-hydroxyquinoline (43 mg, 0.296 mmol) in DMF (3 ml) was added potassium carbonate (82 mg, 0.593 mmol) at room temperature. The reaction mixture was stirred for 30 minutes. 1-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide was added and the resulting mixture was stirred for 6 h at 70° C. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (8 g) chromatography eluting with chloroform/methanol (100:1 to 30:1) to give 1-[(2S,3R)-2-benzyloxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide (1) (62.5 mg, 48.9%).

Workup

  1. stirringthe resulting mixture was stirred for 6 h at 70° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel (8 g) chromatography
  7. washeluting with chloroform/methanol (100:1 to 30:1)

Sources & evidence

ORD record
ord-b6b01da65d2d42bd83c4e36ff946cf1e
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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