HCID 86698827, compound → HCID 86698829, compound

HRID 1054837Notes

Reaction equation

HRID 1054837 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[N:7][NH:8]2)=[CH:4][C:3]=1[C:15]#[C:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[N:7][NH:8]2)=[CH:4][C:3]=1[C:15]#[C:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 86698827HCID 86698827, compound

Product 1

HCID 86698829HCID 86698829, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of methyl 6-chloro-5-(phenylethynyl)-1H-indazole-3-carboxylate (20 mg, 0.064 mmol) in methanol (1 mL) was treated with 10 N aqueous sodium hydroxide (2 drops) and stirred at room temperature for 16 hours. The reaction mixture was then treated with additional 10 N aqueous sodium hydroxide (2 drops) and heated to 70° C. for two hours. The cooled reaction mixture was evaporated in vacuo, and treated with 1 N citric acid. The resulting solids were collected by filtration, dried and purified using prep-HPLC to afford the title compound (1 mg). MS (ES+) 374.9 (M+DMSO)+. Retention time: 1.8 min; Xbridge C18 5 μm 4.6×50 mm, 95% H2O/5% MeCN linear to 5% H2O/95% MeCN over 4.0 min, HOLD at 5% H2O/95% MeCN to 5.0 min. (0.03% NH4OH). Flow: 2.0 mL/min.

Workup

  1. temperatureheated to 70° C. for two hours
  2. customThe cooled reaction mixture
  3. customwas evaporated in vacuo
  4. additiontreated with 1 N citric acid
  5. filtrationThe resulting solids were collected by filtration
  6. customdried
  7. custompurified

Sources & evidence

ORD record
ord-6555dfb0ea05493f9404307ae1ee1475
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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