Acetyl chloride → CPG-52852

HRID 1920276Notes

Reaction equation

HRID 1920276 reaction equation
C(Cl)(=O)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:15]([CH2:26][CH3:27])=[N:14][C:13]=1[C:28]#[N:29]>C(O)C>[NH2:29][C:28]1[C:13]2[N:14]=[C:15]([CH2:26][CH3:27])[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:12]=2[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58500142HCID 58500142, compound

Product 1

HCID 10309114CPG-52852

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of acetyl chloride (0.15 mL, 2 mmol) in ethanol (2 mL) was added to a solution of N-{4-[5-(2-aminophenyl)-4-cyano-2-ethyl-1H-imidazo 1-yl]butyl}methanesulfonamide (0.19 g) in ethanol (4 mL). The mixture was heated at reflux for two hours, allowed to cool to room temperature, and concentrated under reduced pressure. The resulting off-white solid was dissolved in water (2.0 mL) with heating to 60° C. The resulting solution was adjusted to pH 12 with the addition of 10% w/w sodium hydroxide (about 0.2 mL). The mixture was cooled overnight at 5° C. The crystals were collected by filtration, washed with water, and dried under vacuum at 40° C. for two hours to provide N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide as beige crystals, mp 202° C. to 204° C., having a 1H NMR spectrum consistent with an authentic sample.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for two hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting off-white solid was dissolved in water (2.0 mL)
  5. temperaturewith heating to 60° C
  6. additionThe resulting solution was adjusted to pH 12 with the addition of 10% w/w sodium hydroxide (about 0.2 mL)
  7. temperatureThe mixture was cooled overnight at 5° C
  8. filtrationThe crystals were collected by filtration
  9. washwashed with water
  10. customdried under vacuum at 40° C. for two hours

Sources & evidence

ORD record
ord-d145b8eb0a7f4f21869eada2857f27ec
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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