Trimethylsilyl isocyanate → HCID 58869094, compound

HRID 1623117Notes

Reaction equation

HRID 1623117 reaction equation
C[Si]([N:5]=[C:6]=[O:7])(C)C.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:29][CH2:30][CH3:31])[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][O:27][CH3:28])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1.N12CCCN=C1CCCCC2>ClCCl.C(=O)(O)[O-].[Na+]>[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:29][CH2:30][CH3:31])[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]([O:27][CH3:28])[C:6]([NH2:5])=[O:7])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 3

HCID 70696Trimethylsilyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86612249HCID 86612249, compound

Product 1

HCID 58869094HCID 58869094, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-16 °C

Procedure

Trimethylsilyl isocyanate (0.250 mL, 1.85 mmol) was added dropwise to a solution of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-O-methyl-hydroxylamine in dichloromethane (10 mL) cooled to −16° C. The reaction temperature was cooled to −20° C. over 10 minutes. After stirring for 1.5 hours, the reaction was warmed to 0° C. and stirred for an additional hour. A drop of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.250 mL, 1.85 mmol) was added to the reaction mixture and stirred for 3 days. The reaction mixture was diluted with dichloromethane (50 mL) and saturated aqueous sodium bicarbonate and stirred for 30 minutes. The layers were separated, and the organic layer was dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 0.82 g of 1-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-methoxyurea as off-white crystals, mp 179-181° C. MS (APCI) m/z 371 (M+H+); Anal. calcd for C19H26N6O2: C, 61.36; H, 7.09; N, 22.60. Found: C, 61.08; H, 7.41; N, 22.69.

Workup

  1. temperatureThe reaction temperature was cooled to −20° C. over 10 minutes
  2. temperaturethe reaction was warmed to 0° C.
  3. stirringstirred for an additional hour
  4. stirringstirred for 3 days
  5. stirringstirred for 30 minutes
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bb6fb18f5214d5d950c52d4e5986adc
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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