Acetone → 4-[2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine

HRID 450142Notes

Reaction equation

HRID 450142 reaction equation
CS[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1.[O-][Mn](=O)(=O)=O.[K+].[O-:37][S:38]([O-:40])=O.[Na+].[Na+].[CH3:43]C(C)=O>CC(O)=O.O.C(Cl)(Cl)Cl>[CH3:43][S:38]([C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([NH:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1)(=[O:40])=[O:37]

Participants

8

Reactant 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 498689434-[2-(methylsulfanyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine

Product 1

HCID 498689444-[2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amineYield 31%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 0.421 g (1 mmol) of 4-[2-(methylsulfanyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine (from Example 4) in 130 mL acetone and 20 mL HOAc was treated with 1 g KMnO4 in 10 mL water at room temperature. After 30 min, the reaction was decolorized with aq. Na2SO3 solution and the acetone was removed under vacuum. The residue was diluted with water and the pH adjusted to neutral to give a precipitate which was dissolved in CHCl3 and dried. Chromatography on alumina, eluting with CHCl3/EtOAc (9:1) gave 140 mg (31%) of 4-[2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine: mp (MeOH) 208-211° C.; 1H NMR (CDCl3) 8.88 (br s, 1H), 8.38 (dd, J=4.7, 1.4 Hz, 1H), 8.26 (d, J=7.9 Hz, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.77 (dd, J=7.3, 1.2 Hz, 1H), 7.46-7.38 (m, 3H; 2H after D2O exchange), 7.31 (dd, J=8.3, 4.7 Hz, 1H), 4.08 (m, 2H), 3.83 (m, 2H), 3.76 (m, 4H), 3.62 (s, 3H); Anal. Calcd. for C20H20N8O3S 0.5H2O: C, 52.0; H, 4.6; N, 24.3. Found: C, 51.8; H, 4.6; N, 24.3%.

Workup

  1. customthe acetone was removed under vacuum
  2. additionThe residue was diluted with water
  3. customto give a precipitate which
  4. customdried
  5. washChromatography on alumina, eluting with CHCl3/EtOAc (9:1)

Sources & evidence

ORD record
ord-b6cc6c54fd07459aa72702c4137e223c
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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