Potassium Carbonate → HCID 69678167, compound

HRID 1072060Notes

Reaction equation

HRID 1072060 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].S(C1C=CC(C)=CC=1)(O[CH2:26][C:27]([F:30])([F:29])[F:28])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OC(=O)C)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][CH2:26][C:27]([F:30])([F:29])[F:28])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 69678940HCID 69678940, compound

Product 1

HCID 69678167HCID 69678167, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1-[(2S,3R)-2-hydroxy-5-(2-hydroxyphenyl)-3-pentyl]imidazole-4-carboxamide (10 mg), 2,2,2-trifluoroethyl tosylate (27.4 mg) and potassium carbonate (14.9 mg) in N,N-dimethylformamide (1 ml) was stirred at 130° C. for 13 hours. The mixture was taken up in ethylacetate, washed three times with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (10:1) to give a pale brown powder of 1-{(2S,3R)-2-hydroxy-5-[2-(2,2,2-trifluoroethoxy)phenyl]-3-pentyl}imidazole-4-carboxamide (7) (7.0 mg).

Workup

  1. washwashed three times 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 (10:1)

Sources & evidence

ORD record
ord-bbe13871479d494b807ff270bef7b2c6
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

Loading…