Isopropyl Isothiocyanate → HCID 58833640, compound

HRID 2203549Notes

Reaction equation

HRID 2203549 reaction equation
[CH:1]([N:4]=[C:5]=[S:6])([CH3:3])[CH3:2].[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:29][O:30][CH2:31][CH3:32])[N:20]([CH2:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])([CH3:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])=[CH:11][C:10]=2[N:9]=1>ClCCl>[NH2:7][C:8]1[C:17]2[N:18]=[C:19]([CH2:29][O:30][CH2:31][CH3:32])[N:20]([CH2:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])([CH3:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[S:6])=[CH:11][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 75263Isopropyl IsothiocyanateHCID 68972044HCID 68972044, compound

Product 1

HCID 58833640HCID 58833640, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Isopropyl isothiocyanate (255 μL, 2.38 mmol) was added to a stirred suspension of N-{2-[4-amino-7-(6-aminohexyloxy)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}acetamide (prepared as described in Part I of Example 49, 1.02 g, 2.17 mmol) in dichloromethane (100 mL) at 0° C. The mixture was stirred for 30 minutes at 0° C., then was allowed to warm to room temperature and was stirred over the weekend. The solution was concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution with 7.5-10% methanol in dichloromethane) followed by recrystallization from acetonitrile. The crystals were dissolved in 1:1 dichloromethane/methanol and the resulting solution was concentrated under reduced pressure to afford a white powder that was dried under vacuum at 60° C. to yield 0.43 g of N-(2-{4-amino-2-(ethoxymethyl)-7-[(6-{[(isopropylamino)carbonothioyl]amino}hexyl)oxy]-1H-imidazo[4,5-c]quinolin-1-yl}-1,1-dimethylethyl)acetamide as a white powder, mp 110-120° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred over the weekend
  3. concentrationThe solution was concentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography (silica gel, gradient elution with 7.5-10% methanol in dichloromethane)
  5. customfollowed by recrystallization from acetonitrile
  6. dissolutionThe crystals were dissolved in 1:1 dichloromethane/methanol
  7. concentrationthe resulting solution was concentrated under reduced pressure
  8. customto afford a white powder that
  9. customwas dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-72962d6913e54d56b29949c3721c7b62
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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