N-Methylbenzylamine → HCID 49868947, compound

HRID 450146Notes

Reaction equation

HRID 450146 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:23]([F:25])[F:24])[N:3]=1.[CH3:26][NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCOCC1.O>[CH2:28]([N:27]([CH3:26])[C:2]1[N:3]=[C:4]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH:23]([F:25])[F:24])[N:5]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[N:7]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 7669N-MethylbenzylamineHCID 220368724-(4-chloro-6-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine

Product 1

HCID 49868947HCID 49868947, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole (92 mg, 0.25 mmol) and N-methylbenzylamine (76 mg, 0.625 mmol) in dioxane (5 mL) was heated to reflux for 5 min and cooled. The mixture was diluted with water to give a white precipitate, which was recrystallised from EtOH to give N-benzyl-4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 147-150° C.; 1H NMR (CDCl3) (rotamers) δ 8.45 and 8.22 (2d, J=7.6 and 7.9 Hz, 1H), 7.90 and 7.85 (2d, J=8.3 and 7.7 Hz, 1H), 7.68 and 7.44 (2t, JHF=53.7 and 53.6 Hz, 1H), 7.43-7.25 (m, 7H), 4.92 and 4.90 (2s, 2H), 3.95-3.73 (m, 8H), 3.22 and 3.20 (2s, 3H); Anal. Calc. for C23H23F2N7O: C, 61.2; H, 5.1; N, 21.7. Found: C, 61.45; H, 5.2; N, 21.95%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 min
  3. temperaturecooled
  4. customto give a white precipitate, which
  5. customwas recrystallised from EtOH

Sources & evidence

ORD record
ord-837348f291c944909bc5b30a6b2c1187
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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