Methyl iodide → HCID 178504147, compound

HRID 1404854Notes

Reaction equation

HRID 1404854 reaction equation
[CH3:1][N:2]([CH3:37])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12]/[N:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=4)[N:22]=3)=[CH:17][CH:16]=2)=[S:11])=[CH:5][CH:4]=1.I[CH3:39]>CCO>[CH3:1][N:2]([CH3:37])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][N:13]=[CH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]([F:34])([F:36])[F:35])=[CH:28][CH:27]=4)[N:22]=3)=[CH:19][CH:20]=2)=[SH:11][CH3:39])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 88590243HCID 88590243, compound

Product 1

HCID 178504147HCID 178504147, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution containing (E)-N-(4-(dimethylamino)phenyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (150 mg, 0.285 mmol) and iodomethane (0.054 mL, 0.856 mmol) in EtOH (5 mL) was heated at 80° C. for 3 h before the solvent was removed under reduced pressure. The residue was purified via normal phase flash chromatography (gradient elution with hexanes/EtOAc) to afford the title compound as an orange foam (93 milligrams (mg), 60%): 1H NMR (400 MHz, DMSO-d6) δ 8.61 (s, 1H), 8.48 (s, 1H), 8.22 (d, J=8.24 Hz, 2H), 8.17 (s, 1H), 7.89 (d, J=8.24 Hz, 2H), 7.80 (d, J=8.28 Hz, 2H), 7.41 (d, J=8.28 Hz, 2H), 7.19 (d, J=8.24 Hz, 2H), 6.71 (d, J=8.24 Hz, 2H), 2.99 (s, 6H), 2.42 (s, 3H); EIMS m/z 540 (M+).

Workup

  1. customwas removed under reduced pressure
  2. customThe residue was purified via normal phase flash chromatography (gradient elution with hexanes/EtOAc)

Sources & evidence

ORD record
ord-7382ee890dd5484ebcc9e6a3abb72e1f
Source dataset
uspto-grants-2014_12
Patent number
US08916183B2

Reaction notes

Loading…