Iodoethane → 2-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-ethyl-1H-benzo[d]imidazole

HRID 2202828Notes

Reaction equation

HRID 2202828 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]4[NH:23][C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1.[CH2:28](I)[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]4[N:23]([CH2:28][CH3:29])[C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 715503742-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

Product 1

HCID 715505172-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-ethyl-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Example 107 (13 mg, 0.036 mmol), ethyl iodide (5.6 mg, 0.036 mmol), and cesium carbonate (58 mg, 0.18 mmol) were combined in degassed DMF (1 mL) and heated at 60° C. for 30 min. The mixture was cooled to room temperature, filtered and purified by reverse phase HPLC, providing Example 114 as a solid. 1H NMR: (400 MHz, d6-DMSO) δ 7.71-7.67 (m, 2H), 7.37-7.30 (m, 2H) 6.56 (s, 1H), 4.62-4.58 (m, 3H), 4.47-4.44 (m, 2H), 4.30 (q, J=7.2 Hz, 2H), 2.77 (s, 3H), 2.45 (s, 3H), 2.29 (s, 3H), 1.34 (t, J=7.1 Hz, 3H) ppm; MS: m/z=389.4 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-267a359c969240b783ddd6389fcacc5a
Source dataset
uspto-grants-2016_06
Patent number
US09365562B2

Reaction notes

Loading…