Lithium Hydroxide → HCID 59596375, compound

HRID 2264611Notes

Reaction equation

HRID 2264611 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24](=[O:36])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[CH2:19][CH2:18]3)[N:11]=[CH:10][N:9]=1)=[O:7])C>C1COCC1>[F:34][C:32]([F:33])([F:35])[C:28]1[CH:27]=[C:26]([NH:25][C:24]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([O:14][C:12]4[N:11]=[CH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:13]=4)=[CH:23][CH:22]=3)[CH2:18][CH2:19]2)=[O:36])[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 675312166-[1-(3-trifluoromethyl-phenylcarbamoyl)-2,3-dihydro-1H-indol-5-yloxy]-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 59596375HCID 59596375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.9 ml LiOH (1 M in H2O) are added to a solution of 2.80 g (5.9 mMol) 6-[1-(3-trifluoromethyl-phenylcarbamoyl)-2,3-dihydro-1H-indol-5-yloxy]-pyrimidine-4-carboxylic acid ethyl ester in 20 ml THF. After 1 h at rt, the mixture is concentrated under reduced pressure, the residue re-dissolved in EtOAc and 1 M HCl, the aqueous layer separeted off and extracted twice with EtOAc. The organic phases are washed twice with 1 M HCl, water and brine, dried (Na2SO4) and concentrated to the title compound: MS: [M−1]=443; HPLC: AtRet=12.9.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. dissolutionthe residue re-dissolved in EtOAc
  3. extractionextracted twice with EtOAc
  4. washThe organic phases are washed twice with 1 M HCl, water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to the title compound

Sources & evidence

ORD record
ord-e6a142b682044e28a0c2b32f970ea07c
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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