Potassium Carbonate → HCID 69677929, compound

HRID 1072058Notes

Reaction equation

HRID 1072058 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].[ClH:22].[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][Cl:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:28].[ClH:22].[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][CH2:27][CH2:26][CH2:25][N:24]([CH3:29])[CH3:23])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 69678940HCID 69678940, compound

Product 1

HCID 69677929HCID 69677929, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-[(2S,3R)-2-hydroxy-5-(2-hydroxyphenyl)-3-pentyl]imidazole-4-carboxamide (20 mg), 3-(dimethylamino)propyl chloride hydrochloride (32.7 mg) and potassium carbonate (38 mg) in N,N-dimethylformamide (3 ml) was stirred overnight at 60° C. The mixture was evaporated. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane, triethylamine, and methanol (20:1:4) and the product was treated with HCl in EtOAc to give a pale brown oil of 1-{(2S,3R)-2-hydroxy-5-[2-(3-dimethylaminopropoxy)phenyl]-3-pentyl}imidazole-4-carboxamide dihydrochloride (5) (21.2 mg).

Workup

  1. customThe mixture was evaporated
  2. customThe residue was purified by column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane, triethylamine, and methanol (20:1:4)
  4. additionthe product was treated with HCl in EtOAc

Sources & evidence

ORD record
ord-69314accd3b8424aa84104f8e58fcb3c
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

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