HCID 57786383, compound → HCID 57785846, compound

HRID 1399257Notes

Reaction equation

HRID 1399257 reaction equation
[CH2:1]([Zn]CC)C.[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:25]([CH3:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=4[Cl:28])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH:29]([OH:33])[CH2:30][CH:31]=[CH2:32])=[CH:9][CH:8]=1>ClCCl.[Cl-].[NH4+]>[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:25]([CH3:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=4[Cl:28])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([CH:29]([OH:33])[CH2:30][CH:31]2[CH2:1][CH2:32]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 57786383HCID 57786383, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 57785846HCID 57785846, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Under nitrogen atmosphere, diethyl zinc (1 M solution in hexane, 0.800 mL, 0.800 mmol) was added to a solution of 1-[9-chloro-1-(2,4-dichloro-6-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]but-3-en-1-ol (70.0 mg, 0.160 mmol) in dichloromethane (3.2 mL) at 0° C., and then diiodemethane (0.129 mL, 1.60 mmol) was added at 0° C. The resultant mixture was stirred at room temperature for 2 hr, 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 a solid, which was recrystallized from ethyl acetate/hexane to afford the title compound as a colorless solid (24.6 mg, 00540 mmol, 34%).

Workup

  1. additiondiiodemethane (0.129 mL, 1.60 mmol) was added at 0° C
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture
  8. customto give a solid, which
  9. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-77fd8fb92eeb4759bd6fe6ce5f93b693
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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