3-Pyridinemethanamine → HCID 49869922, compound

HRID 450150Notes

Reaction equation

HRID 450150 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.[NH2:26][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>O1CCOCC1.O>[F:24][CH:23]([F:25])[C:15]1[N:14]([C:4]2[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=[C:2]([NH:26][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[N:3]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1

Participants

5

Reactant 2

HCID 310183-PyridinemethanamineHCID 220368724-(4-chloro-6-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine

Product 1

HCID 49869922HCID 49869922, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole (0.183 g, 0.5 mmol) and 3-aminomethylpyridine (0.135 g, 1.25 mmol) in 10 mL dioxane was heated under gentle reflux for 5 min. After cooling, the mixture was diluted with water to give an oily solid, which was recrystallized from MeOH to give 0.13 g (59% yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinylmethyl)-1,3,5-triazin-2-amine: mp 160-161° C.; 1H NMR (CDCl3) (rotamers) δ 8.61 (d, J=4.4 Hz, 1H), 8.42 and 8.32 (2d, J=7.6 and 8.4 Hz, 1H), 7.89-7.87 (m, 1H), 7.70 (dt, J=7.7, 1.65 Hz, 1H), 7.65 and 7.59 (2t, JHF=53.7 and 53.5 Hz, 1H), 7.43-7.37 (m, 2H), 7.34 (br t, J=8.7 Hz, 1H), 7.24 (br t, J=6.2 Hz, 1H), 6.55 and 6.41 (2 m, exchangeable with D2O, 1H), 4.82 and 4.78 (2 d, J=5.3 and 5.1 Hz, 2H), 3.88 (m, 4H), 3.78 (m, 4H); Anal. Calcd. for C21H20F2N8O: C, 57.5; H, 4.6; N, 25.6. Found: C, 57.7; H, 4.5; N, 25.7%.

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 5 min
  3. temperatureAfter cooling
  4. customto give an oily solid, which
  5. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-e50ba4c62ae94dc4b991f668f5a768ee
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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