Triethylamine → 4-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline

HRID 606055Notes

Reaction equation

HRID 606055 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][O:31][CH2:32][CH3:33])[N:24]([CH2:25][CH2:26][CH2:27][C:28]#[CH:29])[C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:13]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][O:31][CH2:32][CH3:33])[N:24]([CH2:25][CH2:26][CH2:27][C:28]3[O:1][N:2]=[C:3]([C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH:29]=3)[C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756315N-hydroxybenzenecarboximidoyl chlorideHCID 866168754-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 866168774-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

N-Hydroxybenzenecarboximidoyl chloride (prepared as described in Part A of Example 2, 2.61 g, 16.8 mmol) was added to a solution of 4-chloro-2-(ethoxymethyl)-1-pent-4-ynyl-1H-imidazo[4,5-c]quinoline (prepared as described in Part F of Example 6, 2.90 g, 8.39 mmol) and triethylamine (3.50 mL, 25.2 mmol) in dichloromethane at 6° C. The solution was heated at 50° C. under a nitrogen atmosphere for 4 hours. The solution was diluted with dichloromethane, transferred to a separatory funnel, washed with water and brine, dried over sodium sulfate, filtered, and concentrated to an oil. The oil was triturated with hexanes and the solvent was decanted. The oil was triturated with diethyl ether and a solid formed that was isolated by filtration to provide 4-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (1.98 g). The filtrate was purified by flash chromatography (silica gel, gradient elution from 7:3 to 1:1 hexanes/ethyl acetate) to provide an additional 0.24 g of product. The total amount of 4-chloro-2-(ethoxymethyl)-1-[3-(3-phenylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline isolated was 2.22 g.

Workup

  1. customtransferred to a separatory funnel
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe oil was triturated with hexanes
  7. customthe solvent was decanted
  8. customThe oil was triturated with diethyl ether
  9. customa solid formed that
  10. customwas isolated by filtration

Sources & evidence

ORD record
ord-bdd0e9b37e9948108bfa60eef5fd5968
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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