Triethylamine → HCID 11474441, compound

HRID 1907958Notes

Reaction equation

HRID 1907958 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:23]2[N:24]=[C:25]([CH2:32][O:33][NH2:34])[N:26]([CH2:27][C:28]([CH3:31])([OH:30])[CH3:29])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1>CN(C=O)C>[NH2:13][C:14]1[C:23]2[N:24]=[C:25]([CH2:32][O:33][NH:34][S:9]([CH3:8])(=[O:11])=[O:10])[N:26]([CH2:27][C:28]([OH:30])([CH3:31])[CH3:29])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 11370084HCID 11370084, compound

Product 1

HCID 11474441HCID 11474441, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.634 mL, 4.55 mmol) and methanesulfonyl chloride (0.211 mL, 2.73 mmol) were added to a solution of 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (prepared as described in Example 100, 685 mg, 2.27 mmol) in DMF (5 mL). A solid formed immediately. The mixture was stirred for 3.5 hours at room temperature, then additional triethylamine (0.634 mL) and methanesulfonyl chloride (0.211 mL) were added. The reaction mixture was stirred for an additional 1.5 hours, then was partitioned between water (20 mL) and dichloromethane (30 mL). The aqueous layer was extracted with dichloromethane (2×30 mL). The organic layers were combined and allowed to stand overnight at room temperature. Crystals formed and were isolated by filtration to provide 40 mg of N-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}methanesulfonamide. Additional crystals were isolated from the mother liquor after a seed crystal was added. The two crops were combined and dried in a vacuum oven to provide 160 mg of N-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}methanesulfonamide as pale yellow crystals, mp 232-234° C.

Workup

  1. customA solid formed immediately
  2. stirringThe reaction mixture was stirred for an additional 1.5 hours
  3. customwas partitioned between water (20 mL) and dichloromethane (30 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (2×30 mL)
  5. waitto stand overnight at room temperature
  6. customCrystals formed
  7. customwere isolated by filtration

Sources & evidence

ORD record
ord-bd41c7b53d1f4180aa1b9d52aab61e62
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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