Trityl chloride → HCID 118451583, compound

HRID 522824Notes

Reaction equation

HRID 522824 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C(N(CC)CC)C.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[CH2:22]([O:21][CH2:20][C:13]1[N:14]([CH2:15][C:16]([CH3:19])([OH:17])[CH3:18])[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH:1][C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:11]=2[N:12]=1)[CH3:23]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 159603Resiquimod

Product 1

HCID 118451583HCID 118451583, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Amino-2-(ethoxymethyl)-α,α-dimethyl-1H-Imidazo[4,5-c]quinoline-1-ethanol (CAN 144875-48-9, 1.6 g, 5.09 mmol) was combined with acetonitrile (60 mL) to give a white suspension. Then triethylamine (1.77 mL, 12.7 mmol) and trityl chloride (1.7 g, 6.11 mmol) were added under Argon with stirring. The reaction mixture was irradiated in a microwave reactor at 100° C. for 30 minutes. Upon stirring the mixture the product precipitated and was isolated by filtration at 0° C., washed with cold acetonitrile and dried to yield the title compound (2.37 g, 83%) as white solid; MS (ESI): 557.5 (MH+).

Workup

  1. customto give a white suspension
  2. customThe reaction mixture was irradiated in a microwave reactor at 100° C. for 30 minutes
  3. stirringUpon stirring the mixture the product
  4. customprecipitated
  5. customwas isolated by filtration at 0° C.
  6. washwashed with cold acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-3a39756da2864368ad67d2b86d94e096
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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