Lithium Hydroxide → HCID 18449886, compound

HRID 16981Notes

Reaction equation

HRID 16981 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([CH3:33])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[O:20])=[CH:16][C:15]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:14]2)[CH:8]=1)C.[Li+].[OH-]>CO>[C:29]([C:15]1[CH:16]=[C:17]([NH:18][C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[O:20])[N:13]([C:9]2[CH:8]=[C:7]([CH2:6][CH:5]([CH3:33])[C:4]([OH:34])=[O:3])[CH:12]=[CH:11][CH:10]=2)[N:14]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58842829HCID 58842829, compound

Product 1

HCID 18449886HCID 18449886, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 202 (15 mg, mmol) and 2N LiOH (3 mL) in MeOH (3 mL) was stirred at RT overnight. The reaction mixture was adjusted to pH=4, extracted with ethyl acetate (3×20 mL), the combined organic extracts were washed with brine, dried (Na2SO4), and filtered. After the filtrate was concentrated, the residue was purified by preparative-TLC to afford 3-(3-{3-t-butyl-5-[3-(4-chloro-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-2-methyl-propionic acid as a racemate (13 mg, 90%). 1H NMR (DMSO): 12.48 (br s, 1H), 9.35 (br s, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.34-7.32 (m, 2H), 7.26 (d, J=8.4 Hz, 1H), 7.24 (d, J=8.8 Hz, 2H), 7.10 (d, J=7.6 Hz, 1H), 6.45 (s, 1H), 2.74 (m, 1H), 2.65 (m, 1H), 2.31 (m, 2H), 1.26 (s, 9H), 0.99 (d, J=6.8 Hz, 3H); MS (ESI) m/z: 455 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationAfter the filtrate was concentrated
  6. customthe residue was purified by preparative-TLC

Sources & evidence

ORD record
ord-657764942d4841fab9a09c1af9eded33
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Reaction notes

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