Trimethylsilyl isocyanate → HCID 86612267, compound

HRID 1623204Notes

Reaction equation

HRID 1623204 reaction equation
[CH3:1][Si:2]([N:5]=[C:6]=[O:7])([CH3:4])[CH3:3].[CH3:8][O:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:28])[C:18]=2[N:17]=[C:16]1[CH3:29]>N12CCCN=C1CCCCC2.ClCCl>[NH2:28][C:19]1[C:18]2[N:17]=[C:16]([CH3:29])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:10]([O:9][CH3:8])[C:6]([NH:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 86612266HCID 86612266, compound

Product 1

HCID 86612267HCID 86612267, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl isocyanate (1.62 mL, 12.0 mmol) and 1,8-diazabicyclo[5.4.0]undec-7ene (one drop) were added to a solution of 1-[4-(methoxyamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (3.00 g, 10.0 mmol) in dichloromethane (100 mL). The reaction mixture was stirred overnight at room temperature, then concentrated under reduced pressure to afford 4.1 g of crude N-[4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxy-N′-(trimethylsilyl)urea, which was used without purification in the next step.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5caf6a3ccee54fdabf8cbe215d4edd41
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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