Hydrochloric Acid → (1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)cyclobutyl)methanone

HRID 707355Notes

Reaction equation

HRID 707355 reaction equation
COC[N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]([CH:15]1[CH2:18][CH:17]([NH:19][C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16]1)=[O:14].Cl>O1CCCC1>[NH:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[C:13]([CH:15]1[CH2:18][CH:17]([NH:19][C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16]1)=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86694210(1-(methoxymethyl)-1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)-cyclobutyl)methanone

Product 1

HCID 86694211(1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)cyclobutyl)methanoneYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1-(methoxymethyl)-1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)-cyclobutyl)methanone (534 mg, 1.40 mmol) in tetrahydrofuran (20 mL) at room temperature was added concentrated hydrochloric acid (20 mL). The reaction mixture was stirred at room temperature for 1 hour and then heated at 60° C. for 6 hours. The mixture was partially concentrated, neutralized with aqueous saturated sodium bicarbonate and diluted with ethyl acetate. The aqueous phase was extracted with ethyl acetate (2×40 mL) and the combined organic extracts were washed with brine (20 mL). The organic was dried over magnesium sulfate and concentrated to get a residue, which was purified by flash column chromatography on silica gel (10% to 40% ethyl acetate in petroleum ether) to give (1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)cyclobutyl)methanone (0.57 g, 1.30 mmol, 92% yield) as solid.

Workup

  1. temperatureheated at 60° C. for 6 hours
  2. concentrationThe mixture was partially concentrated
  3. additiondiluted with ethyl acetate
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×40 mL)
  5. washthe combined organic extracts were washed with brine (20 mL)
  6. dry with materialThe organic was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto get a residue, which
  9. customwas purified by flash column chromatography on silica gel (10% to 40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-479a49aacd7746eba2635c48b4c7174e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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