HCID 57785864, compound → HCID 57786162, compound

HRID 1399064Notes

Reaction equation

HRID 1399064 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH:30]=[O:31])=[C:10]2[C:14]=1[N:13]=[C:12]1[N:15]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[C:26]([F:29])([F:28])[F:27])[CH2:16][CH2:17][CH2:18][N:11]21>O1CCCC1>[Cl:5][C:6]1[C:14]2[N:13]=[C:12]3[N:15]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[C:26]([F:28])([F:27])[F:29])[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH:30]([OH:31])[CH2:1][CH3:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 57785864HCID 57785864, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 57786162HCID 57786162, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (3.0 M solution in diethyl ether, 0.35 mL, 1.05 mmol) was added to a stirred solution of 9-chloro-1-[4-chloro-2-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (400 mg, 0.966 mmol) in tetrahydrofuran (3.0 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction was quenched by water, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from ethanol to give the title compound as a colorless crystal (411 mg, 0.925 mmol, 96%).

Workup

  1. customThe reaction was quenched by water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1854be09921f4fbea638f796e1a456d2
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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