Sodium Hydroxide → HCID 21183693, compound

HRID 1385103Notes

Reaction equation

HRID 1385103 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:21]=[C:20]3[C:16]([C:17]([CH2:27][CH3:28])=[N:18][N:19]3[CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[CH:22]1([N:19]2[C:20]3[C:16](=[CH:15][CH:14]=[C:13]([C:11]([NH:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:29])=[O:2])=[CH:9][CH:8]=4)=[O:12])[CH:21]=3)[C:17]([CH2:27][CH3:28])=[N:18]2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53932397HCID 53932397, compound

Product 1

HCID 21183693HCID 21183693, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 380 mg (0.971 mmol, 1.0 equiv) 4-[(1-cyclopentyl-3-ethyl-1H-indazole-6-carbonyl)-amino]-benzoic acid methyl ester, 4 mL 1N NaOH and 20 mL methanol was heated to reflux for 40 minutes. After cooling to room temperature, the reaction mixture was concentrated on a rotary evaporator, and the residue diluted with 150 mL H2O, acidified to pH=1, and extracted 2×50 mL ethyl acetate. The organic extracts were combined, washed 1×25 mL each H2O, brine, and dried over Na2SO4. Filtration, concentration of filtrate, and drying at high vacuum, room temperature gave 298 mg (81%) of a white crystalline solid: mp 249-251° C.; Anal. calcd for C22H23N3O3: C, 70.00; H, 6.14; N, 11.13. Found: C, 69.66; H, 6.13; N, 11.08.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 40 minutes
  3. concentrationthe reaction mixture was concentrated on a rotary evaporator
  4. additionthe residue diluted with 150 mL H2O
  5. extractionextracted 2×50 mL ethyl acetate
  6. washwashed 1×25 mL each H2O, brine
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration, concentration of filtrate
  9. customdrying at high vacuum, room temperature

Sources & evidence

ORD record
ord-825e08010a0f4cb3baf7336c12450815
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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