Water → 1-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]-N-(2,2,2-trifluoroethyl)propan-1-amine

HRID 1399320Notes

Reaction equation

HRID 1399320 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([NH2:26])[CH2:24][CH3:25])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.FC(F)(F)S(O[CH2:42][C:43]([F:46])([F:45])[F:44])(=O)=O.O>CN(C)C=O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([NH:26][CH2:42][C:43]([F:46])([F:45])[F:44])[CH2:24][CH3:25])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate2×HCID 81531DiisopropylethylamineHCID 577863351-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-amine

Product 1

HCID 577861181-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]-N-(2,2,2-trifluoroethyl)propan-1-amineYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-amine (200 mg, 0.488 mmol) and ethyldiisopropylamine (0.166 mL, 0.976 mmol) in N,N-dimethylformamide (10 mL) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.0774 mL, 0.54 mmol) at room temperature. The mixture was stirred at room temperature for 20 hr. To the reaction mixture was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.030 mL, 0.208 mmol) at room temperature and the mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on NH-silica gel eluting with a 25-45% ethyl acetate/n-hexane gradient mixture to give the title compound (76.4 mg, 0.155 mmol, 32%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on NH-silica gel eluting with a 25-45% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-f2f1db7926214f47b08f278a0e6a9c9c
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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