Water → HCID 58102802, compound

HRID 450144Notes

Reaction equation

HRID 450144 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][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.C(Cl)Cl>O1CCOCC1>[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]([N:27]([CH3:26])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:3]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7515N-MethylanilineHCID 220368724-(4-chloro-6-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine

Product 1

HCID 58102802HCID 58102802, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 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-methylaniline (67 mg, 0.625 mmol) in dioxane (5 mL) was heated under reflux for 1 hr and cooled. Dilution with water gave a precipitate, which was collected and dried. Chromatography on SiO2 eluting with CH2Cl2 gave 70 mg (64% yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-phenyl-1,3,5-triazin-2-amine: mp (hexanes) 160-162° C.; 1H NMR (CDCl3) δ 8.04 (m, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.49 (t, J=7.6 Hz, 2H), 7.45-7.06 (m, 7H), 3.91 (m, 4H), 3.81 (m, 4H), 3.56 (s, 3H); Anal. Calc. for C22H21F2N7O: C, 60.4; H, 4.8; N, 22.4. Found: C, 60.2; H, 5.0; N, 22.5%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperaturecooled
  4. customwas collected
  5. customdried

Sources & evidence

ORD record
ord-4b5c7a9b8d1f4145bda7a932a95451ff
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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