Triethylamine → HCID 16224483, compound

HRID 1930100Notes

Reaction equation

HRID 1930100 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:31][CH3:32])[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1.Cl[C:34]([O:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:35]>CN1C(=O)CCC1.O>[CH2:31]([C:20]1[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH:8][C:34](=[O:35])[O:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:18]=2[N:19]=1)[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 10309114CPG-52852

Product 1

HCID 16224483HCID 16224483, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Triethylamine (1.93 mL, 5 eq) was added to a chilled (ice/water bath) suspension of N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide (1.0 g, 1 eq) in NMP (6.0 mL). n-Butyl chloroformate (1.13 g, 3 eq) was added dropwise. The reaction mixture was allowed to come to ambient temperature and stirred for 24 hours. The reaction mixture was diluted with cold water (25 mL) and then extracted with dichloromethane (50 mL). The organic layer was washed sequentially with water (2×50 mL), 4% sodium carbonate (50 mL), water (50 mL), and brine (50 mL) and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica gel eluted with a linear gradient of 0-25% CMA in chloroform, 2000 mL) followed by recrystallization from acetonitrile to provide 0.35 g of butyl 2-ethyl-1-{4-[(methylsulfonyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-ylcarbamate as a white solid, mp 164-166° C. Anal calcd for C22H31N5O4S: C, 57.25; H, 6.77; N, 15.17. Found: C, 57.13; H, 6.61; N, 15.20.

Workup

  1. temperaturea chilled
  2. customto come to ambient temperature
  3. extractionextracted with dichloromethane (50 mL)
  4. washThe organic layer was washed sequentially with water (2×50 mL), 4% sodium carbonate (50 mL), water (50 mL), and brine (50 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by automated flash chromatography (silica gel
  7. washeluted with a linear gradient of 0-25% CMA in chloroform
  8. custom2000 mL) followed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-89021feb5dc44f489da8abf700233b26
Source dataset
uspto-grants-2012_05
Patent number
US08188111B2

Reaction notes

Loading…