Methyl iodide → HCID 52932155, compound

HRID 877375Notes

Reaction equation

HRID 877375 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][CH:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]2[NH:19][N:18]=[N:17][N:16]=2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:26]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:13][CH:14]([C:15]2[N:19]([CH3:26])[N:18]=[N:17][N:16]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:12])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178439104HCID 178439104, compound

Product 1

HCID 52932155HCID 52932155, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution 2-(4-isopropylphenyl)-N-[phenyl(1H-tetrazol-5-yl)methyl]acetamide (34.0 mg, 0.101 mmol) in 0.5 ml of anhydrous DMF was added K2CO3 (14.0 mg, 0.101 mmol) and MeI (0.006 ml, 0.101 mmol). The resulting solution was stirred at RT for 3 hour. Filtered and the residue was purified by preparative HPLC (5-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 8.0 mg (23%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.342 (m, 3H); 7.226 (m, 2H), 7.172 (ABq, J=8.2 Hz, 4H), 6.894 (br d, J=7.6 Hz, 1H), 6.424 (d, J=7.9 Hz, 1H), 3.910 (s, 3H), 3.587 (s, 2H), 2.888 (sept, J=7.0 Hz, 1H), 1.234 (d, J=7.0 Hz, 6H). ES-MS [M+1]+: 350.2.

Workup

  1. filtrationFiltered
  2. customthe residue was purified by preparative HPLC (5-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Sources & evidence

ORD record
ord-eddac98a08a246a2b8d3042f032e0be7
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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