Sodium Hydroxide → HCID 89783358, compound

HRID 1056138Notes

Reaction equation

HRID 1056138 reaction equation
C(OC([NH:8][CH:9]([C:11]1[NH:12][C:13]([C:21]2[C:30]([F:31])=[CH:29][CH:28]=[C:27]3[C:22]=2[N:23]=[C:24]([NH:33][CH:34]2[CH2:36][CH2:35]2)[C:25]([CH3:32])=[N:26]3)=[CH:14][C:15]=1[C:16]([O:18]CC)=[O:17])[CH3:10])=O)(C)(C)C.Cl.O1CCOCC1.[OH-].[Na+]>O1CCOCC1.O>[NH2:8][CH:9]([C:11]1[NH:12][C:13]([C:21]2[C:30]([F:31])=[CH:29][CH:28]=[C:27]3[C:22]=2[N:23]=[C:24]([NH:33][CH:34]2[CH2:36][CH2:35]2)[C:25]([CH3:32])=[N:26]3)=[CH:14][C:15]=1[C:16]([OH:18])=[O:17])[CH3:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 89783722HCID 89783722, compound

Product 1

HCID 89783358HCID 89783358, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel (80 mL) was charged with ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (284a) (0.41 g, 0.81 mmol) and LiOH monohydrate (Sigma-Aldrich) (342 mg, 8.16 mmol) in 1,4-Dioxane (12 mL) and water (10 mL). The reaction mixture was stirred and heated in a CEM Voyager Microwave (Large-Scale Unit) at 120° C. for 35 min (100 watts, Powermax feature off). This material was transferred to a 150-mL round-bottomed flask for next step in the reaction. m/z (ESI, +ve) 470 (M+H). To the mixture from step 1, was added 4 M HCl/1,4-dioxane (Sigma-Aldrich) until pH 2-3. The mixture was stirred at RT for 4 h. The mixture was neutralized with 5 N NaOH (pH 7). The precipitate was collected by filtration and the solids were washed with hexanes. This gave 2-(1-aminoethyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid (284b; 285 mg, 0.77 mmol, 95% yield) as light yellow solid. m/z (ESI, +ve) 353 (M-NH2)′.

Workup

  1. customA glass microwave reaction vessel (80 mL)
  2. customThis material was transferred to a 150-mL round-bottomed flask for next step in the reaction
  3. stirringThe mixture was stirred at RT for 4 h
  4. filtrationThe precipitate was collected by filtration
  5. washthe solids were washed with hexanes

Sources & evidence

ORD record
ord-00f33a1cb2d34076a7aa02c69aef8de0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…