Ethanolamine → HCID 178488983, compound

HRID 1067399Notes

Reaction equation

HRID 1067399 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[NH:16][CH:17]=[C:18]([C:20](O)=[O:21])[N:19]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:35]([CH2:37][NH2:38])[OH:36].O>CN(C=O)C>[OH:36][CH2:35][CH2:37][NH:38][C:20]([C:18]1[N:19]=[C:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[NH:16][CH:17]=1)=[O:21]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 178488985HCID 178488985, compound

Product 1

HCID 178488983HCID 178488983, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-Cyclopentyloxy-4-methoxyphenyl)-imidazole-4-carboxylic acid (500 mg, 1.65 mmol) in DMF (15 ml) at room temperature was added carbonyldiimidazole (295 mg, 1.8 mmol). The resultant solution was stirred for 30 minutes and then ethanolamine (180 μl, 1.8 mmol) was added and the reaction mixture stirred at room temperature overnight. Water (75 ml) was added and the mixture extracted with ethyl acetate (2×75 ml). The combined organics were washed with brine (40 ml), dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2; CH2Cl2:EtOH (95:5) (1% NH3)) afforded 2-(3-cyclopentyloxy-4-methoxyphenyl)-imidazole-4-carboxylic acid, N-(2-hydroxyethyl) amide (247 mg, 43%) as a white solid, mp 206-208° C.

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×75 ml)
  2. washThe combined organics were washed with brine (40 ml)
  3. dry with materialdried over Na2SO4
  4. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-f85b9edf460347c884f958d225189aa1
Source dataset
uspto-grants-2001_06
Patent number
US06248769B1

Reaction notes

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