HCID 86698827, compound → HCID 86698829, compound

HRID 338493Notes

Reaction equation

HRID 338493 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 10N aqueous sodium hydroxide (2 drops) and stirred at room temperature for 16 hours. The reaction mixture was then treated with additional 10N aqueous sodium hydroxide (2 drops) and heated to 70° C. for two hours. The cooled reaction mixture was evaporated in vacuo, and treated with 1N 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 1N citric acid
  5. filtrationThe resulting solids were collected by filtration
  6. customdried
  7. custompurified

Sources & evidence

ORD record
ord-91bb4305e3b14e46b4370b8e4f8058c0
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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