Sodium Nitrite → HCID 178497313, compound

HRID 1403528Notes

Reaction equation

HRID 1403528 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]([N:19]3[CH2:23][CH2:22][CH2:21][C@@H:20]3[CH3:24])=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:15]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[N:29]([O-])=O.[Na+]>Cl.O>[NH:8]1[C:7]2[CH:6]=[CH:5][C:4]([C:9]3[C:18]([N:19]4[CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:24])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:15]=4)[N:10]=3)=[CH:3][C:2]=2[N:1]=[N:29]1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 70664863(S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 178497313HCID 178497313, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-methyl 2-(3,4-diaminophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (600 mg, crude) in HCl (60 mL, 2N) was added sodium nitrite (164.7 mg, 2.39 mmol) in water (1 mL) dropwise at 0-5° C. The resulting solution was stirred for 15 min at 0° C., then diluted with water (150 mL), extracted with dichloromethane (3×80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (1.25% methanol in dichloromethane) to afford (S)-methyl 2-(1H-benzo[d][1,2,3]triazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (130 mg).

Workup

  1. extractionextracted with dichloromethane (3×80 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified via silica gel chromatography (1.25% methanol in dichloromethane)

Sources & evidence

ORD record
ord-774e96a2a1e646cabcd170a2e068ac3f
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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