Ammonium Chloride → (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 1403527Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:14]=3)[N:9]=2)=[CH:4][C:3]=1[N+:28]([O-])=O.[NH4+].[Cl-]>CO.[Fe]>[NH2:28][C:3]1[CH:4]=[C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:14]=3)[N:9]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (1.0 g, 2.45 mmol) in methanol (40 mL) was added Fe (1.38 g, 24.6 mmol) and NH4Cl (1.3 g, 24.30 mmol). After the resulting solution was stirred for 6 h at 60° C., the solids were filtered out. The filtrate was concentrated under vacuum and dissolved in water (200 mL), extracted with dichloromethane (3×80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as yellow solid (970 mg, crude).

Workup

filtrationthe solids were filtered out
concentrationThe filtrate was concentrated under vacuum
dissolutiondissolved in water (200 mL)
extractionextracted with dichloromethane (3×80 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6bb684154dc74ebfa1aa56846bac0f9e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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