Ethanolamine → HCID 25174615, compound

HRID 1097304Notes

Reaction equation

HRID 1097304 reaction equation
C(O[C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[N: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]=[N: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 25174611HCID 25174611, compound

Product 1

HCID 25174615HCID 25174615, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

4-[3-(3-Pyrazol-1-yl-phenyl)-imidazo[1,2-b]pyridazin-7-yl]-benzoic acid ethyl ester (Ex. 34) (1 eq, 0.073 mmol, 30 mg) and ethanol amine (10 eq, 0.73 mmol, 0.04 ml) are dissolved in EtOH (2 ml) and K2CO3 (1.5 eq, 0.11 mmol, 15.1 mg) is added. The reaction mixture is stirred for 5 h at 55° C. The solvent is then 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-b]-pyridazin-7-yl]-benzamide as a yellow solid; [M+H]+=425

Workup

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

Sources & evidence

ORD record
ord-ccbeff6476b744f4b9841b2d3d43f1b9
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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