Ammonia → HCID 59026668, compound

HRID 606121Notes

Reaction equation

HRID 606121 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:29][CH2:30][CH3:31])[N:14]([CH2:15][CH2:16][C:17]3[O:21][N:20]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH:18]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:32]>CO>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[CH:18]=[C:17]([CH2:16][CH2:15][N:14]3[C:10]4[C:9]5[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=5[N:3]=[C:2]([NH2:32])[C:11]=4[N:12]=[C:13]3[CH2:29][CH2:30][CH3:31])[O:21][N:20]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86616898HCID 86616898, compound

Product 1

HCID 59026668HCID 59026668, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-1-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline (1.22 g, 2.81 mmol) and 7 N ammonia in methanol (100 mL) was sealed in a pressure vessel and heated at 150° C. for 12 hours and allowed to cool to room temperature. The volatiles were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel (eluting with 10% to 15% CMA in chloroform). The product was then triturated sequentially with toluene and hexane/diethyl ether to provide 0.312 g of 1-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 208.0-209.0° C.

Workup

  1. customwas sealed in a pressure vessel
  2. temperatureto cool to room temperature
  3. customThe volatiles were removed under reduced pressure
  4. customthe crude product was purified by column chromatography on silica gel (eluting with 10% to 15% CMA in chloroform)
  5. customThe product was then triturated sequentially with toluene and hexane/diethyl ether

Sources & evidence

ORD record
ord-d461fa63887447c2b8dcecc00d176468
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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