Isopropyl iodide → HCID 57786297, compound

HRID 1399187Notes

Reaction equation

HRID 1399187 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:16]=[CH:17][C:18]([OH:22])=[N:19][C:20]=4[CH3:21])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([O:28][CH:29]([F:31])[F:30])[C:24]([F:27])([F:26])[F:25])=[CH:4][CH:3]=1.I[CH:33]([CH3:35])[CH3:34]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:20]([CH3:21])=[N:19][C:18]([O:22][CH:33]([CH3:35])[CH3:34])=[CH:17][CH:16]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([O:28][CH:29]([F:30])[F:31])[C:24]([F:27])([F:26])[F:25])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 178433442HCID 178433442, compound

Product 1

HCID 57786297HCID 57786297, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-{9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl}-6-methylpyridin-2-ol (30.0 mg, 0.0648 mmol) in toluene (1.0 mL) was added silver carbonate (35.7 mg, 0.130 mmol) and 2-iodopropane (32.3 μL, 0.324 mmol). The reaction mixture was stirred at room temperature for 5 hrs. The starting material wasn't consumed completely. The mixture was stirred at 50° C. for 5 hrs. After cooling the mixture was filtered through on the pad of celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography eluting with a 0-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (29.3 mg, 0.0633 mmol, 98%).

Workup

  1. customThe starting material wasn't consumed completely
  2. stirringThe mixture was stirred at 50° C. for 5 hrs
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered through on the pad of celite
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 0-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-2696c6d8e1af4b139e3ee57a62777a23
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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