HCID 57786179, compound → HCID 57785917, compound

HRID 1628744Notes

Reaction equation

HRID 1628744 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH:27]=[O:28])=[C:10]2[C:14]=1[N:13]=[C:12]1[N:15]([C:19]3[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][N:20]=3)[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[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][N:20]=4)[CH2:16][CH2:17][CH2:18][N:11]3[C:10]=2[C:9]([CH:27]([OH:28])[CH2:1][CH3:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 57786179HCID 57786179, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 57785917HCID 57785917, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethylmagnesium bromide (3.0 M solution in diethyl ether, 51 μL, 0.153 mmol) was added to a stirred solution of 9-chloro-1-(3,5-dichloropyridin-2-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (53.7 mg, 0.141 mmol) in tetrahydrofuran (1.0 mL) at 0° C., and the mixture was stirred at 0° C. for 50 min. The reaction was quenched by aqueous saturated ammonium chloride, 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 to give the title compound as a colorless solid (57.8 mg, 0.141 mmol, 100%).

Workup

  1. customThe reaction was quenched by aqueous saturated ammonium chloride
  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

Sources & evidence

ORD record
ord-afd3685acd034f6bae5fc57819659e5f
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…