HCID 57786105, compound → HCID 57786383, compound

HRID 1628904Notes

Reaction equation

HRID 1628904 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:24]=[O:25])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=3[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]21.[CH2:26]([Mg]Br)[CH:27]=[CH2:28]>O1CCCC1.[Cl-].[NH4+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=4[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:24]([OH:25])[CH2:28][CH:27]=[CH2:26])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 57786105HCID 57786105, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 57786383HCID 57786383, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of 9-chloro-1-(2,4-dichloro-6-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (200 mg, 0.507 mmol) in tetrahydrofuran (5 mL) was added dropwise allylmagnesium bromide (1 M solution in diethyl ether, 1.00 mL, 1.00 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give the two title compounds as colorless solids.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture
  7. customto give the two title compounds as colorless solids

Sources & evidence

ORD record
ord-190df97a69ec42e59b79ad178b414de3
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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