Tetrahydrofuran → HCID 44156498, compound

HRID 1399180Notes

Reaction equation

HRID 1399180 reaction equation
C[C:2]1([C:5]([C:7]2[C:12]3[N:13]4[CH2:19][CH2:18][CH2:17][N:16]([C:20]5[C:21]([CH3:28])=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=5)[C:14]4=[N:15][C:11]=3[C:10]([Cl:29])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3]1.O1[CH2:34][CH2:33][CH2:32]C1>>[Cl:29][C:10]1[C:11]2[N:15]=[C:14]3[N:16]([C:20]4[C:21]([CH3:28])=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)[CH2:17][CH2:18][CH2:19][N:13]3[C:12]=2[C:7]([C:5]([CH:2]2[CH2:3][CH2:4]2)([CH:32]2[CH2:33][CH2:34]2)[OH:6])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 68908686HCID 68908686, compound

Product 1

HCID 44156498HCID 44156498, compoundYield 70%

Procedure

To a solution of methyl [9-chloro-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl](cyclopropyl)methanone (145.7 mg, 0.365 mmol) in tetrahydrofuran (2.0 mL) was added c-propylmagnesium bromide (1.0 M solution in tetrahydrofuran, 3.42 mL, 3.420 mmol). The reaction mixture was stirred at room temperature for 2 hrs. After cooling, the mixture was quenched with aqueous saturated ammonium chloride and extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-55% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from hexane to give the title compound as a solid (105.5 mg, 0.240 mmol, 70%).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was quenched with aqueous saturated ammonium chloride
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 0-55% ethyl acetate/n-hexane gradient mixture
  10. customThe resulting solid was recrystallized from hexane

Sources & evidence

ORD record
ord-a25d80f8ad484f8bacb95bdc5a5419a7
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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