Methyl iodide → HCID 178484778, compound

HRID 1190116Notes

Reaction equation

HRID 1190116 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([NH:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[NH:24][C:25]([C:27]2[NH:28][CH:29]=[C:30]([C:32]#[N:33])[N:31]=2)=[O:26])=[CH:4][CH2:3]1.IC.[C:37]([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:17]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH3:37])([CH3:15])[CH3:16])[CH:11]=[CH:10][C:9]=2[NH:24][C:25]([C:27]2[NH:28][CH:29]=[C:30]([C:32]#[N:33])[N:31]=2)=[O:26])=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 178424522HCID 178424522, compound

Product 1

HCID 178484778HCID 178484778, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-cyano-1H-imidazole-2-carboxylic acid {2-(4,4-dimethyl-cyclohex-1-enyl)-4-[1-(2-methanesulfonyl-ethylamino)-1-methyl-ethyl]-phenyl}-amide (as prepared in Example 18, 8.0 mg, 0.017 mmol), iodomethane (25 μL, 0.40 mmol) and solid NaHCO3 (25 mg, 0.30 mmol) in 1.0 mL of THF was stirred at RT for 6 h. The solvent was removed by evaporation and the residue was purified by silica gel chromatography (0-2% MeOH/DCM) to afford the title compound (5.0 mg, 61%) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): δ 11.90 (s, 1H), 9.63 (s, 1H), 8.31 (d, 1H, J=8.6 Hz), 7.75 (s, 1H), 7.41 (dd, 1H, J=8.6, 2.3 Hz), 7.28 (d, 1H, J=2.3 Hz), 5.77 (m, 1H), 3.11 (t, 2H, J=7.1 Hz), 2.87 (s, 3H), 2.84 (t, 2H, J=6.0 Hz), 2.29 (m, 2H), 2.24 (s, 3H), 2.11 (m, 2H), 1.60 (t, 2H, J=6.3 Hz), 1.40 (s, 6H), 1.11 (s, 6H). Mass spectrum (ESI-neg, m/z): Calcd. for C26H35N5O3S, 496.3 (M−H). found 496.1.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by silica gel chromatography (0-2% MeOH/DCM)

Sources & evidence

ORD record
ord-d51985018662408c8216eb5133fcd344
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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