Ethanolamine → 1-(4-Chloro-3-trifluoromethylphenyl)-3-{4-[2-(2-hydroxy-ethylamino)-pyrimidin-4-yloxy]-phenyl}-urea

HRID 659006Notes

Reaction equation

HRID 659006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[NH2:33][CH2:34][CH2:35][OH:36]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:33][CH2:34][CH2:35][OH:36])[N:20]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 675239201-(4-Chloro-3-trifluoromethyl-phenyl)-3-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-phenyl]-urea

Product 1

HCID 249976541-(4-Chloro-3-trifluoromethylphenyl)-3-{4-[2-(2-hydroxy-ethylamino)-pyrimidin-4-yloxy]-phenyl}-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 144 mg (0.296 mmol) 1-(4-Chloro-3-trifluoromethyl-phenyl)-3-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-phenyl]-urea, 40 mg (0.65 mmol) 2-aminoethanol and 5 ml THF was stirred at r.t. for 12 h. The reaction mixture was evaporated and the residue purified by chromatography on silica (dichloromethane/ethanol 96:4). Yield 56 mg (40%) of the title compound.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by chromatography on silica (dichloromethane/ethanol 96:4)

Sources & evidence

ORD record
ord-01988608ffef4dc599d62c17321459a5
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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