HCID 57785864, compound → HCID 57786345, compound

HRID 1399065Notes

Reaction equation

HRID 1399065 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH:31]=[O:32])=[C:11]2[C:15]=1[N:14]=[C:13]1[N:16]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[C:27]([F:30])([F:29])[F:28])[CH2:17][CH2:18][CH2:19][N:12]21>O1CCCC1>[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[C:27]([F:28])([F:30])[F:29])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH:31]([CH:1]2[CH2:3][CH2:2]2)[OH:32])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 57785864HCID 57785864, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 57786345HCID 57786345, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylmagnesium bromide (1.0 M solution in tetrahydrofuran, 2.9 mL, 2.9 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 (1.00 g, 2.41 mmol) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. 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. The residue was recrystallized from ethyl acetate to give the title compound as a colorless crystal (567 mg, 1.24 mmol, 51%).

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
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5f0869e0ac9f4566838c643173c4eeaa
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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