1-Chloroethyl chloroformate → HCID 22228444, compound

HRID 1744682Notes

Reaction equation

HRID 1744682 reaction equation
[C:1]([NH:5][C:6]([C:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:13][CH2:12][N:11](C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OC(Cl)C)=O>C1(C)C=CC=CC=1>[C:1]([NH:5][C:6]([C:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22228452HCID 22228452, compound

Product 1

HCID 22228444HCID 22228444, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the product of step C (550 mg; 1.88 mmol) in toluene (10 mL) was added 1-chloroethyl chloroformate (15 mmol; 1.62 mL) and the reaction was heated to reflux for 36 h. The volatiles were removed in vacuo, the crude carbamate was then dissolved in methanol (10 mL) and the resultant solution was heated to reflux for 2 h. The volatiles were removed in vacuo, the crude amine was dissolved in methylene chloride (100 mL) and the solution was washed with a saturated solution of sodium bicarbonate, brine and the compound dried (Na2SO4). The drying agent was removed by filtration and the volatiles were removed in vacuo to furnish the crude product which was purified on silica gel using a gradient elution (95:5 then 90:10 methylene chloride/methanol (containing 10% v/v ammonium hydroxide) to afford the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 36 h
  3. customThe volatiles were removed in vacuo
  4. dissolutionthe crude carbamate was then dissolved in methanol (10 mL)
  5. temperaturethe resultant solution was heated
  6. temperatureto reflux for 2 h
  7. customThe volatiles were removed in vacuo
  8. dissolutionthe crude amine was dissolved in methylene chloride (100 mL)
  9. washthe solution was washed with a saturated solution of sodium bicarbonate, brine
  10. dry with materialthe compound dried (Na2SO4)
  11. customThe drying agent was removed by filtration
  12. customthe volatiles were removed in vacuo
  13. customto furnish the crude product which
  14. customwas purified on silica gel using
  15. washa gradient elution (95:5
  16. addition90:10 methylene chloride/methanol (containing 10% v/v ammonium hydroxide)

Sources & evidence

ORD record
ord-822130b1db494f83bf175caa26e8183f
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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