Iodobenzene → HCID 22254466, compound

HRID 434013Notes

Reaction equation

HRID 434013 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][O:18][CH2:19][C:20]#[CH:21])[C:4]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1.I[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][O:18][CH2:19][C:20]#[C:21][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1

Participants

3

Reactant 2

HCID 11575IodobenzeneHCID 22254454HCID 22254454, compound

Product 1

HCID 22254466HCID 22254466, compoundYield 21.7%

Conditions

Temperature
50 °C

Procedure

Using the general method of Example 12 Part A, 2-methyl-1-[2-(prop-2-ynyloxy)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (0.396 g, 1.392 mmol) was reacted with iodobenzene (0.17 mL, 1.532 mmol) at ambient temperature. After 18 hours the reaction was incomplete. The solution was heated to 50° C. for 3 hours to complete the reaction. The volatiles were removed under reduced pressure. The resulting oil was partitioned between dichloromethane and 4% aqueous sodium carbonate and the organic layer removed. The aqueous layer was extracted with dichloromethane (3×). The organic fractions were combined, dried with anhydrous sodium sulfate and the volatiles were removed under reduced pressure. The resulting oil was purified by chromatography over silica gel (95/5 dichloromethane/methanol). The resulting white solid was dissolved in dichloromethane (2 mL) and reacted with 1M HCl in ether (2 mL). The volatiles were removed under reduced pressure and the resulting solids recrystallized from methanol to provide 0.1089 g of 2-methyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (hydrochloride),.g as a tan solid.

Workup

  1. customthe reaction
  2. customThe volatiles were removed under reduced pressure
  3. customThe resulting oil was partitioned between dichloromethane and 4% aqueous sodium carbonate
  4. customthe organic layer removed
  5. extractionThe aqueous layer was extracted with dichloromethane (3×)
  6. dry with materialdried with anhydrous sodium sulfate
  7. customthe volatiles were removed under reduced pressure
  8. customThe resulting oil was purified by chromatography over silica gel (95/5 dichloromethane/methanol)
  9. dissolutionThe resulting white solid was dissolved in dichloromethane (2 mL)
  10. customreacted with 1M HCl in ether (2 mL)
  11. customThe volatiles were removed under reduced pressure
  12. customthe resulting solids recrystallized from methanol

Sources & evidence

ORD record
ord-bb74002f308a417d94685d4c28152803
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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