Ethanolamine → HCID 25261748, compound

HRID 383272Notes

Reaction equation

HRID 383272 reaction equation
C(O[C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([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:7][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][C:8]([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:7][CH:6]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 25262647HCID 25262647, compound

Product 1

HCID 25261748HCID 25261748, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

4-[3-(3-Pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzoic acid ethyl ester (Ex. 1.11) (1 eq, 0.086 mmol, 35 mg) and ethanol amine (10 eq, 0.86 mmol, 0.05 ml) are dissolved in EtOH (2 ml) and K2CO3 (1.5 eq, 0.128 mmol, 17.7 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)-4-[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-0adf3b11a94344a08bc69b1e5ecbc264
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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