HCID 57786383, compound → HCID 57785846, compound

HRID 1628906Notes

Reaction equation

HRID 1628906 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 23%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Under nitrogen atmosphere, diethyl zinc (1 M solution in hexane, 0.860 mL, 0.860 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 (75.0 mg, 0.172 mmol) in dichloromethane (1.7 mL) at 0° C., and then diiodemethane (0.139 mL, 1.73 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 (17.5 mg, 00388 mmol, 23%).

Workup

  1. additiondiiodemethane (0.139 mL, 1.73 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-d7c6eb01f9f24a1c8d330a5d7b18a31a
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

Loading…