Tetrahydrofuran → HCID 57786074, compound

HRID 1399062Notes

Reaction equation

HRID 1399062 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:31]([O:33]C)=O)=[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.O1C[CH2:38][CH2:37][CH2:36]1>>[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:29])([F:28])[F:30])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([C:31]([OH:33])([CH2:36][CH2:37][CH3:38])[CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 57785993HCID 57785993, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 57786074HCID 57786074, compound

Conditions

Temperature
60 °C

Procedure

n-Propylmagnesium bromide (2.0 M solution in tetrahydrofuran, 3.9 mL, 7.8 mmol) was added to a stirred solution of methyl 9-chloro-1-[4-chloro-2-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (700 mg, 1.58 mmol) in tetrahydrofuran (5.0 mL), and the mixture was stirred at 60° C. for 6 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 purified by preparative HPLC to give a mixture contained an intermediate of the title compound as the trifluoroacetic acid salt. The mixture was washed with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the solid, which was recrystallized from ethanol/ethyl acetate to give the title compound as a colorless crystal (129 mg, 0.258 mmol, 16%).

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 purified by preparative HPLC
  8. customto give a mixture

Sources & evidence

ORD record
ord-521ec2662e614d1ab7d96a42409d1415
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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