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3-Pyridinecarboxaldehyde → HCID 67519540, compound

HRID 1925476
Notes
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Reaction equation

HRID 1925476 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][O:21][CH3:22].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=O)[CH:24]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.CO>[CH3:22][O:21][CH2:20][C:7]1[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:29][C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 67519397HCID 67519397, compound

Product 1

HCID 67519540HCID 67519540, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 887MethanolSolvent

Procedure

To a round-bottomed flask containing 1-(4-aminobutyl)-2-methoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (10.0 g, 33.4 mmol) was added methanol (160 mL) followed by acetic acid (40 mL). The reaction was stirred for 5 minutes and pyridine 3-carboxaldehyde (5.4 g, 50.1 mmol) was added and the reaction was stirred overnight at ambient temperature. Sodium cyanoborohydride (1 M in THF, 33.4 mL, 33.4 mmol) was added to the resultant imine in portions over 10 minutes. After 45 minutes the solvent was evaporated to afford an oil. To the oil was added saturated aqueous sodium bicarbonate (200 mL) and the aqueous layer was washed with ethyl acetate (200 mL) and dichloromethane (200 mL). The product was extracted from the aqueous with 20% methanol (2×100 mL) in dichloromethane. The organic layers were combined and the solvent evaporated to afford crude 2-methoxymethyl-1-{4-[(pyridin-3-ylmethyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-amine (about 2 g). The aqueous layer was again extracted with 20% dimethylformamide (2×100 mL) in dichloromethane. The organic layers were combined and the solvent evaporated to afford crude 2-methoxymethyl-1-{4-[(pyridin-3-ylmethyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-amine (about 2 g).

Workup

  1. stirringthe reaction was stirred overnight at ambient temperature
  2. customAfter 45 minutes the solvent was evaporated
  3. customto afford an oil
  4. washthe aqueous layer was washed with ethyl acetate (200 mL) and dichloromethane (200 mL)
  5. extractionThe product was extracted from the aqueous with 20% methanol (2×100 mL) in dichloromethane
  6. customthe solvent evaporated
  7. customto afford crude 2-methoxymethyl-1-{4-[(pyridin-3-ylmethyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-amine (about 2 g)
  8. extractionThe aqueous layer was again extracted with 20% dimethylformamide (2×100 mL) in dichloromethane
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-f74ad1a193ee48c799b43a35ec26ecc4
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178677B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes