Triethylamine → HCID 57657225, compound

HRID 244878Notes

Reaction equation

HRID 244878 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[N:18]([CH2:19][CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:17]([CH2:26][CH3:27])=[N:16][C:10]=3[C:11]([NH2:15])=[N:12][C:13]=2[CH:14]=1.C(N(CC)CC)C.[CH:35]([N:38]=[C:39]=[O:40])([CH3:37])[CH3:36].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:15][C:11]1[C:10]2[N:16]=[C:17]([CH2:26][CH3:27])[N:18]([CH2:19][CH:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[C:9]=2[C:8]2[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][NH:1][C:39]([NH:38][CH:35]([CH3:37])[CH3:36])=[O:40])=[CH:14][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 61277Isopropyl isocyanateHCID 57657231HCID 57657231, compound

Product 1

HCID 57657225HCID 57657225, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(3-Aminopropyl)-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine (500 mg, 1.4 mmol), triethylamine (410 mg, 4.1 mmol), and isopropyl isocyanate (128 mg, 1.5 mmol) were combined in dichloromethane (50 mL) at 0° C. and the reaction was stirred for approximately 18 hours. Aqueous sodium carbonate (1%, 50 mL) was added and the reaction mixture was stirred for one additional hour. The fractions were separated and the aqueous fraction was extracted with chloroform (3×20 mL). The combined organic fractions were sequentially dried (MgSO4), filtered and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient, 0-20% CMA over 2000 mL). The desired product was further purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 10% methanol in dichloromethane over 1500 mL). A final purification by recrystallization from acetonitrile provided 142 mg of N-{3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propyl}-N′-isopropylurea as a white solid, mp 213-216° C.

Workup

  1. stirringthe reaction mixture was stirred for one additional hour
  2. customThe fractions were separated
  3. extractionthe aqueous fraction was extracted with chloroform (3×20 mL)
  4. dry with materialThe combined organic fractions were sequentially dried (MgSO4)
  5. filtrationfiltered
  6. custompurified by chromatography
  7. washeluting with a CMA
  8. customThe desired product was further purified by chromatography
  9. washa HORIZON HPFC system (silica cartridge, eluting with 10% methanol in dichloromethane over 1500 mL)
  10. customA final purification
  11. customby recrystallization from acetonitrile

Sources & evidence

ORD record
ord-7eca1c6a79b34451ab1941a4ac254415
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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