Ethyl Acetate → HCID 117803009, compound

HRID 520327Notes

Reaction equation

HRID 520327 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[N:8][CH:9]=[CH:10][C:11]=1[Cl:12])(=[O:3])[CH3:2].N12CCCN=C1CCCC[CH2:27]2.[C:37](OCC)(=O)C>C(=O)(OC)OC>[C:1]([O:4][CH2:5][C:6]1[C:7]([C:13]2[N:17]([CH3:27])[C:16]3[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[N:8][CH:9]=[CH:10][C:11]=1[Cl:12])(=[O:3])[CH3:2].[C:1]([O:4][CH2:5][C:6]1[C:7]([C:13]2[N:14]([CH3:37])[C:15]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][C:16]=3[N:17]=2)=[N:8][CH:9]=[CH:10][C:11]=1[Cl:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 117803008HCID 117803008, compound

Product 2

HCID 117803009HCID 117803009, compoundHCID 117803010HCID 117803010, compound

Reagents, catalysts & solvents 1

HCID 12021Dimethyl CarbonateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 160h (500 mg, 1.4 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (212 mg, 1.4 mmol) in dimethyl carbonate (100 mL) was stirred at 140° C. for 3 h. See FIG. 5. TLC (petroleum ether:ethyl acetate=3:1) showed that the starting material was completely consumed. The mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (60 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluting with petroleum ether:ethyl acetate=3:1) to afford (2-(6-(tert-butyl)-1-methyl-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methyl acetate 160i and (2-(5-(tert-butyl)-1-methyl-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methyl acetate 160j as a mixture of regioisomers (480 mg, 92%). MS-ESI: [M+H]+ 372.1.

Workup

  1. customwas completely consumed
  2. additionThe mixture was diluted with water (100 mL)
  3. extractionextracted with EtOAc (100 mL×2)
  4. washThe combined organic layers were washed with brine (60 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (eluting with petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-dfcecd57f50b452ab55dea857884be16
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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