Triethylamine → HCID 67052342, compound

HRID 1907954Notes

Reaction equation

HRID 1907954 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20]Cl)[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:22][N:23]3[C:27](=[O:28])[C:26]4[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:24]3=[O:33])[N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 67052320HCID 67052320, compound2×

Product 1

HCID 67052342HCID 67052342, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (1.00 g, 3.28 mmol) in DMF (3.0 mL) was added to a solution of N-hydroxyphthalimide (642 mg, 3.94 mmol) and triethylamine (0.915 mL, 6.56 mmol) in DMF (3.0 mL). The flask containing the solution of 1-[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol was rinsed with DMF (3.0 mL), which was added to the reaction solution. The solution was stirred at room temperature for 3 hours and a solid formed. The solid was isolated by filtration, washed with dichloromethane, and dried. The off-white solid was dissolved in hot DMF (20 mL). Acetonitrile (50 mL) was added to the solution, which was then placed in a freezer. Crystals formed and were isolated by filtration, washed with acetonitrile, and dried to provide 288 mg of 2-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}-1H-isoindole-1,3(2H)-dione as orange crystals, mp 270-272° C.

Workup

  1. washwas rinsed with DMF (3.0 mL), which
  2. additionwas added to the reaction solution
  3. customa solid formed
  4. customThe solid was isolated by filtration
  5. washwashed with dichloromethane
  6. customdried
  7. dissolutionThe off-white solid was dissolved in hot DMF (20 mL)
  8. additionAcetonitrile (50 mL) was added to the solution, which
  9. customCrystals formed
  10. customwere isolated by filtration
  11. washwashed with acetonitrile
  12. customdried

Sources & evidence

ORD record
ord-4a270a2b2e5d4ff38cbd94874c9aa59f
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

Loading…