Trichloroacetyl isocyanate → HCID 21936611, compound

HRID 432739Notes

Reaction equation

HRID 432739 reaction equation
[O-][N+:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[N:12]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]([CH3:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])[CH:13]=[N:14][C:4]=2[CH:3]=1.ClC(Cl)(Cl)C([N:36]=C=O)=O>ClCCl>[NH2:36][C:3]1[C:4]2[N:14]=[CH:13][N:12]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]([CH3:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])[C:5]=2[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[N:2]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 21936604HCID 21936604, compound

Product 1

HCID 21936611HCID 21936611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the general method of Parts C and D of Example 11, 2-(1H-imidazo[4,5-c]quinolin-1-yl)ethanol (0.63 g, 2.9 mmol) and 5-bromo-N-methyl-N-phenylpentanamide (1.3 g, 4.8 mmol) were combined to provide 0.24 g of 5-[2-(5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]-N-methyl-N-phenylpentanamide as a colorless oil. The resulting N-oxide product was dissolved in dichloromethane and trichloroacetyl isocyanate (0.11 ml) was added dropwise. The reaction was stirred at room temperature for 2 hours and then the solvent was removed under vacuum. The resulting oil was dissolved in methanol and sodium methoxide (0.2 ml, 25% by weight in methanol) was slowly added. The reaction was maintained overnight and then concentrated under vacuum. Purification by flash column chromatography (silica gel, 9:1 ethyl acetate\methanol) provided 24 mg of 5-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]-N-methyl-N-phenylpentanamide as a white solid. 1H NMR (300 MHz, CDCl3) δ7.94 (d, J=8.1 Hz, 1H), 7.83 (m, 2H), 7.52 (dt, J=7.7,1.3 Hz, 1H), 7.41-7.28 (m, 4H), 7.12 (d, J=7.8 Hz, 2H), 5.55 (broad s, 2H), 4.65 (t, J=5.3 Hz, 2H), 3.85 (t, J=5.3 Hz, 2H), 3.31 (t, J=6.3 Hz, 2H), 3.24 (s, 3H), 2.02 (m, 2H), 1.56 (m, 2H), 1.40 (m, 2H); IR (KBr) 3429, 3104, 2946, 2877, 1646, 1595, 1584, 1532, 1496, 1482, 1398, 1360, 1254, 1121, 749, 705 cm−1; MS (EI) m/e 417.2160 (417.2165 calcd for C24H27N5O2).

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe resulting oil was dissolved in methanol
  3. additionsodium methoxide (0.2 ml, 25% by weight in methanol) was slowly added
  4. temperatureThe reaction was maintained overnight
  5. concentrationconcentrated under vacuum
  6. customPurification by flash column chromatography (silica gel, 9:1 ethyl acetate\methanol)

Sources & evidence

ORD record
ord-5d6194a4ca30477d97876cc171d8bdba
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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