Hydrochloric Acid → HCID 67403709, compound

HRID 2102023Notes

Reaction equation

HRID 2102023 reaction equation
C([N:4]1[C:12]2[C:7](=[C:8]([C:15]([F:18])([F:17])[F:16])[C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1)(=O)C.Cl.[OH-].[Na+].CCOC(C)=O>CCO>[F:17][C:15]([F:16])([F:18])[C:8]1[C:9]([C:13]#[N:14])=[CH:10][CH:11]=[C:12]2[C:7]=1[CH:6]=[N:5][NH:4]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67403715HCID 67403715, compound

Product 1

HCID 67403709HCID 67403709, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The crude 1-acetyl-4-(trifluoromethyl)-1H-indazole-5-carbonitrile from Example 210A (ca. 1.28 mmol) was dissolved in EtOH (5 mL) and conc. HCl (5 mL). The resulting mixture was heated to 70° C. for 20 min. The cooled reaction's pH was adjusted to ca. 8 with 6 N NaOH. EtOAc (20 mL) was added and the isolated organic portion was dried (Na2SO4), filtered and concentrated. Purification by semipreparative HPLC afforded the title compound as a pale yellow solid (0.076 g, 28% overall): 1H NMR (DMSO-d6) δ 14.13 (s, 1H), 8.41 (s, 1H), 8.06 (d, J=6.0 Hz, 1H), 7.93 (d, J=6.0 Hz, 1H).

Workup

  1. dry with materialthe isolated organic portion was dried (Na2SO4)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by semipreparative HPLC

Sources & evidence

ORD record
ord-33fef081c7c5480c90e42dbefd487bf2
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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