3-Methoxybenzylamine → HCID 57657272, compound

HRID 244880Notes

Reaction equation

HRID 244880 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[C:7]([CH:19]=O)[CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27]>CO.ClCCl>[CH2:15]([N:14]1[C:10]2[C:9]3[CH:8]=[C:7]([CH2:19][NH:27][CH2:26][C:25]4[CH:28]=[CH:29][CH:30]=[C:23]([O:22][CH3:21])[CH:24]=4)[CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[CH:13]1)[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 211563-MethoxybenzylamineHCID 86629393HCID 86629393, compound

Product 1

HCID 57657272HCID 57657272, compoundYield 9.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-Amino-1-isobutyl-1H-imidazo[4,5-c]quinoline-8-carbaldehyde (237 mg, 0.66 mmol) and 3-methoxybenzylamine (100 mg, 1.3 mmol) were combined in methanol (25 mL) and dichloromethane (1 mL). The solution was purged with nitrogen gas and a 1M solution of sodium cyanoborohydride in THF (2 mL) was added. The reaction was stirred for 30 minutes. Additional sodium cyanoborohydride in THF (1M, 1 mL) was added and the reaction was stirred for an additional 15 minutes. Aqueous sodium carbonate (1%, 0.25 mL) was added and the reaction was stirred for 7 days. The solvent was removed under reduced pressure and approximately equal portions of chloroform and water were added. The fractions were separated and the organic fraction was sequentially dried (MgSO4), filtered, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a CMA:chloroform gradient, 0-20% CMA). Recrystallization from acetonitrile provided 25 mg of 1-isobutyl-8-{[(3-methoxybenzyl)amino]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, mp 125-126° C.

Workup

  1. customThe solution was purged with nitrogen gas
  2. additiona 1M solution of sodium cyanoborohydride in THF (2 mL) was added
  3. additionAdditional sodium cyanoborohydride in THF (1M, 1 mL) was added
  4. stirringthe reaction was stirred for an additional 15 minutes
  5. additionAqueous sodium carbonate (1%, 0.25 mL) was added
  6. stirringthe reaction was stirred for 7 days
  7. customThe solvent was removed under reduced pressure and approximately equal portions of chloroform and water
  8. additionwere added
  9. customThe fractions were separated
  10. dry with materialthe organic fraction was sequentially dried (MgSO4)
  11. filtrationfiltered
  12. custompurified by chromatography
  13. washeluting with a CMA
  14. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-1c2d131c90be45ea8aad7e4a52a1c4c7
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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