Ethanolamine → HCID 68486564, compound

HRID 383271Notes

Reaction equation

HRID 383271 reaction equation
C(O[C:4](=[O:31])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH:30]=[CH:29][CH:28]=[N:27]5)[CH:21]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH:6]=1)C.[CH2:32]([CH2:34][NH2:35])[OH:33].C([O-])([O-])=O.[K+].[K+]>CCO>[OH:33][CH2:32][CH2:34][NH:35][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][N:14]3[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH:30]=[CH:29][CH:28]=[N:27]5)[CH:21]=4)=[CH:18][N:19]=[C:13]3[CH:12]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 25262648HCID 25262648, compound

Product 1

HCID 68486564HCID 68486564, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

3-[3-(3-Pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzoic acid ethyl ester (Ex. 1.10) (1 eq, 0.098 mmol, 40 mg) and ethanol amine (10 eq, 0.98 mmol, 0.06 ml) are dissolved in EtOH (2 ml) and K2CO3 (1.5 eq, 0.147 mmol, 20.3 mg) is added. The reaction mixture is stirred for 5 h at 55° C. The solvent is removed in vacuo and the reaction is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield N-(2-hydroxy-ethyl)-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo-[1,2-a]-pyridin-7-yl]-benzamide as a white solid; [M+H]+=424

Workup

  1. customThe solvent is removed in vacuo
  2. customthe reaction is purified by flash column chromatography
  3. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-274d186cf31343dfb7c3b715f7a2dc2e
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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