Sodium Hydroxide → HCID 21978853, compound

HRID 10297Notes

Reaction equation

HRID 10297 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[NH:17][CH:18]1[CH2:20][CH2:19]1)C.[OH-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[CH:18]1([NH:17][C:6]2[CH:7]=[C:8]([N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[C:9]([F:11])=[CH:10][C:5]=2[C:4]([OH:21])=[O:3])[CH2:19][CH2:20]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 210411862-Cyclopropylamino-5-fluoro-4-pyrrolidin-1-ylbenzoic acid ethyl ester

Product 1

HCID 21978853HCID 21978853, compoundYield 89.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(pyrrolidin-1-yl)-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester (Example 3e, 3.10 g, 10.4 mmol) in methanol (50 mL) and tetrahydrofuran (20 mL) is added 1N solution of sodium hydroxide (35 mL). The reaction mixture is stirred at 80° C. for 20 hours, cooled to room temperature, and diluted with ethyl acetate. The organic layer is washed with 1N hydrochloric acid, water, and brine. The organic layer is dried over MgSO4, filtered, and the filtrate concentrated to afford the title compound as a solid (2.47 g). MS CI: m/z 263 (M+).

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with 1N hydrochloric acid, water, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ce8ce431edd04053a879283a27982b23
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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