Iodoethane → (S)-2-sec-Butylamino-6-(1-ethyl-1H-tetrazol-5-yl)-isonicotinic acid methyl ester

HRID 1436591Notes

Reaction equation

HRID 1436591 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][NH:13][N:14]=2)[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:28][CH3:29]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:14]([CH2:28][CH3:29])[N:13]=[N:12][N:11]=2)[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 68815560(S)-2-sec-Butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl ester

Product 1

HCID 68814499(S)-2-sec-Butylamino-6-(1-ethyl-1H-tetrazol-5-yl)-isonicotinic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of (S)-2-sec-butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl ester (720 mg, 2.61 mmol) in DMF (10 mL) with potassium carbonate (541 mg, 3.92 mmol) and iodoethane (0.364 mL, 3.92 mL) at room temperature. Dilute with ethyl acetate (100 mL), wash with water (twice), saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give approximately a 1:1 mixture of the two title compounds which are used directly in the next step without further purification.

Workup

  1. washwash with water (twice), saturated aqueous sodium chloride
  2. dry with materialdry (sodium sulfate)
  3. concentrationconcentrate
  4. customto give approximately
  5. additiona 1:1 mixture of the two title compounds which
  6. customare used directly in the next step without further purification

Sources & evidence

ORD record
ord-83b68017f95a47f7925e542eee82260e
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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