Sodium Hydroxide → HCID 86698826, compound

HRID 338491Notes

Reaction equation

HRID 338491 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]CC)=[O:12])=[N:7][NH:8]2)=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.[OH-].[Na+]>C(O)C>[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:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86698824HCID 86698824, compound

Product 1

HCID 86698826HCID 86698826, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 6-chloro-5-[4-(morpholin-4-yl)phenyl]-1H-indazole-3-carboxylate (72 mg, 0.19 mmol) in ethanol (2 mL) was added 6N aqueous sodium hydroxide (0.5 mL, 3.0 mmol). The mixture was stirred for three hours at 70° C. The cooled reaction mixture was neutralized with Dowex acid resin concentrated in vacuo. The crude product was purified by reverse phase column (water/acetonitrile, 0-40%, 20CV) to give the title compound (21 mg).

Workup

  1. customThe cooled reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by reverse phase column (water/acetonitrile, 0-40%, 20CV)

Sources & evidence

ORD record
ord-a36ebd15f2e542beafca6e64a90e8e2d
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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