HCID 53979019, compound → HCID 21183687, compound

HRID 1385115Notes

Reaction equation

HRID 1385115 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:24][CH3:25])=[N:15][N:16]2[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9])C>C(O)C.[OH-].[Na+]>[CH:19]1([N:16]2[C:17]3[C:13](=[CH:12][CH:11]=[C:10]([C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:26])=[O:3])=[O:9])[CH:18]=3)[C:14]([CH2:24][CH3:25])=[N:15]2)[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 1

HCID 53979019HCID 53979019, compound

Product 1

HCID 21183687HCID 21183687, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 330 mg (0.923 mmol, 1.0 equiv) 3-[(1-cyclopentyl-3-ethyl-1H-indazole-6-carbonyl)-amino]-propionic acid ethyl ester in 10 mL ethanol and 4 mL 1N NaOH was heated to reflux for 1 h. After cooling to room temperature, the reaction mixture was concentrated, diluted with 75 mL H2O, acidified to pH 1, and extracted 3×35 mL ethyl acetate. The organic extracts were combined, washed 1×25 mL H2O, 1×25 mL brine, and dried over Na2SO4. Filtration, concentration of filtrate on a rotary evaporator and drying at high vacuum, room temperature gave 297 mg (98%) of white solid: mp 151-153° C.; Anal. calcd for C18H23N3O3: C, 65.63; H, 7.04; N, 12.76. Found: C, 65.75; H, 7.12; N, 12.91.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. concentrationthe reaction mixture was concentrated
  4. additiondiluted with 75 mL H2O
  5. extractionextracted 3×35 mL ethyl acetate
  6. washwashed 1×25 mL H2O, 1×25 mL brine
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration, concentration of filtrate
  9. customon a rotary evaporator
  10. customdrying at high vacuum, room temperature

Sources & evidence

ORD record
ord-5b481f98b6f440c68baa814f0a5e66ce
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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