Triethylamine hydrochloride → (S)-2-sec-Butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl ester

HRID 732445Notes

Reaction equation

HRID 732445 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[N:7]=[C:6]([NH:12][C@H:13]([CH2:15][CH3:16])[CH3:14])[CH:5]=1.[N-:18]=[N+:19]=[N-:20].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]2[N:18]=[N:19][NH:20][N:11]=2)[N:7]=[C:6]([NH:12][C@H:13]([CH2:15][CH3:16])[CH3:14])[CH:5]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 68814564(S)-2-sec-Butylamino-6-cyano-isonicotinic acid methyl ester

Product 1

HCID 68815560(S)-2-sec-Butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl esterYield 65.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat a suspension of (S)-2-sec-butylamino-6-cyano-isonicotinic acid methyl ester (932 mg, 4.0 mmol), sodium azide (780 mg, 12 mmol), and triethylamine hydrochloride (1.65 g, 12 mmol) in toluene (13 mL) at 90° C. for 2 days. Cool to room temperature and extract with water (3×30 mL), acidify the combined aqueous layers to about pH=2 using 1 N HCl, extract the desired product with ethyl acetate (4×50 mL), dry (sodium sulfate) and concentrate to give the title compound (720 mg, 65%).

Workup

  1. temperatureHeat
  2. extractionextract with water (3×30 mL)
  3. extractionextract the desired product with ethyl acetate (4×50 mL)
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-33c5f2a4966d40ae93ca481664a4b94a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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