Water → HCID 58833734, compound

HRID 540894Notes

Reaction equation

HRID 540894 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[CH3:8][O:9][CH2:10][CH2:11][C:12]1[N:13]([CH2:33][CH2:34][CH3:35])[C:14]2[C:23]3[CH:22]=[CH:21][C:20]([O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[CH:19][C:18]=3[N:17]=[C:16]([NH2:31])[C:15]=2[N:32]=1.O>C(Cl)(Cl)Cl.C(O)C>[NH2:31][C:16]1[C:15]2[N:32]=[C:12]([CH2:11][CH2:10][O:9][CH3:8])[N:13]([CH2:33][CH2:34][CH3:35])[C:14]=2[C:23]2[CH:22]=[CH:21][C:20]([O:24][CH:25]3[CH2:26][CH2:27][N:28]([C:6]([NH2:5])=[O:7])[CH2:29][CH2:30]3)=[CH:19][C:18]=2[N:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 70696Trimethylsilyl isocyanateHCID 68972633HCID 68972633, compound

Product 1

HCID 58833734HCID 58833734, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

Trimethylsilylisocyanate (0.225 mL, 1.67 mmol) was added dropwise to a slurry of 2-(2-methoxyethyl)-7-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-ylamine (prepared as described in Part A of Example 388, 0.640 g, 1.67 mmol) in chloroform (16 mL) at 0° C. The reaction mixture was stirred for 40 minutes and water (10 mL) was added. The reaction mixture was stirred vigorously for 2 hours, diluted with 200 mL ethanol, and then concentrated under reduced pressure to approximately 100 mL. Another 100 mL ethanol was added and the solution was evaporated to afford a white solid that was recrystallized from ethanol to provide 0.625 g of 4-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}piperidine-1-carboxamide as granular off-white crystals, mp 207-208.5° C.

Workup

  1. customprepared
  2. customat 0° C
  3. stirringThe reaction mixture was stirred vigorously for 2 hours
  4. concentrationconcentrated under reduced pressure to approximately 100 mL
  5. additionAnother 100 mL ethanol was added
  6. customthe solution was evaporated
  7. customto afford a white solid
  8. customthat was recrystallized from ethanol

Sources & evidence

ORD record
ord-1c6c552e62064a9bb73b58f9f7357047
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

Loading…