Potassium Carbonate → HCID 12970025, compound

HRID 278498Notes

Reaction equation

HRID 278498 reaction equation
[OH:1][C@H:2]([C@H:4]([N:14]1[CH:18]=[C:17]([C:19]([NH2:21])=[O:20])[N:16]=[CH:15]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH3:3].Br[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[OH:1][C@H:2]([C@H:4]([N:14]1[CH:18]=[C:17]([C:19]([NH2:21])=[O:20])[N:16]=[CH:15]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 69678940HCID 69678940, compound

Product 1

HCID 12970025HCID 12970025, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[(2S,3R)-2-hydroxy-5-(2-hydroxyphenyl)-3-pentyl]imidazole-4-carboxamide (obtained in Example 23(4)) (4.1 mg), 1-bromo-3-phenylpropane (7 mg), and potassium carbonate (4 mg) in N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. The mixture was taken up in ethyl acetate, washed twice with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (20:1) to give a colorless gummy oil of 1-{(2S,3R)-2-hydroxy-5-[2-(3-phenylpropoxy)phenyl]-3-pentyl}imidazole-4-carboxamide (4.9 mg).

Workup

  1. washwashed twice with water
  2. customdried
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (20:1)

Sources & evidence

ORD record
ord-9e646ee6b50741e19557cb80d61b69c8
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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