Methyl iodide → 2-(4-methoxyphenyl)-N-(3-(2-methyl-2H-tetrazol-5-yl)thiophen-2-yl)acetamide

HRID 1519968Notes

Reaction equation

HRID 1519968 reaction equation
IC.[N:3]1[NH:4][N:5]=[N:6][C:7]=1[C:8]1[CH:12]=[CH:11][S:10][C:9]=1[NH:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[C:25](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:14]([NH:13][C:9]2[S:10][CH:11]=[CH:12][C:8]=2[C:7]2[N:3]=[N:4][N:5]([CH3:25])[N:6]=2)=[O:24])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 46869224N-(3-(2H-tetrazol-5-yl)thiophen-2-yl)-2-(4-methoxyphenyl)acetamide

Product 1

HCID 468692252-(4-methoxyphenyl)-N-(3-(2-methyl-2H-tetrazol-5-yl)thiophen-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.20 ml, 3.21 mmol) was added to a heterogeneous mixute of N-(3-(2H-tetrazol-5-yl)thiophen-2-yl)-2-(4-methoxyphenyl)acetamide (Example 8.1., 620 mg, 1.97 mmol) and potassium carbonate (1.36 g, 9.84 mmol) in DMF (10 ml). After stirring for 72 h, the solution was diluted with water and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was directly purified by HPLC to yield 2-(4-methoxyphenyl)-N-(3-(2-methyl-2H-tetrazol-5-yl)thiophen-2-yl)acetamide. Method [7] Retention time 6.03 min by HPLC (MH+ 330). 1H NMR (300 MHz, CDCl3) δ 10.59 (s, 1H), 7.34 (d, J=6.0 Hz, 1H), 7.33 (d, J=8.7 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 6.91 (d, J=6.0 Hz, 1H), 4.28 (s, 3H), 3.89 (s, 3H), 3.86 (s, 2H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was directly purified by HPLC

Sources & evidence

ORD record
ord-f2eb034c4d0f4623b0c2ecd346c3c347
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

Loading…