Lithium Hydroxide → HCID 45110614, compound

HRID 1690510Notes

Reaction equation

HRID 1690510 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:15]2[N:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=[C:18]3[C:23]=2[CH:22]=[CH:21][CH:20]=[CH:19]3)=[O:13])=[CH:7][CH:6]=1)C.[OH-].[Li+]>C1COCC1.CO>[CH:30]1([N:14]([C:15]2[N:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=[C:18]3[C:23]=2[CH:22]=[CH:21][CH:20]=[CH:19]3)[C:12](=[O:13])[NH:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:36])=[O:3])=[CH:10][CH:9]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66905365HCID 66905365, compound

Product 1

HCID 45110614HCID 45110614, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-[3-cyclohexyl-3-(2-phenyl-2H-indazol-3-yl)-ureido]-benzoic acid ethyl ester (10 mg, 21 μmol in THF/MeOH 2/1 (150 μl) was a added a 1 N aqueous lithium hydroxide solution (120 μl, 120 μmmol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred for 12 h at ambient temperature, poured onto ice water/1 N aqueous HCl solution 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (10 mg, 22 umol; quant.) as yellow solid. MS: m/e=455.4 [M+H+].

Workup

  1. additionpoured onto ice water/1 N aqueous HCl solution 1/1
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-45c1d13e2c3e4342b7813a7875d09c21
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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