Triethylamine → HCID 11314674, compound

HRID 1907959Notes

Reaction equation

HRID 1907959 reaction equation
C(N(CC)CC)C.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.[NH2:14][C:15]1[C:24]2[N:25]=[C:26]([CH2:33][O:34][NH2:35])[N:27]([CH2:28][C:29]([CH3:32])([OH:31])[CH3:30])[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1>CN(C=O)C>[NH2:14][C:15]1[C:24]2[N:25]=[C:26]([CH2:33][O:34][NH:35][C:11]([CH:8]3[CH2:10][CH2:9]3)=[O:12])[N:27]([CH2:28][C:29]([OH:31])([CH3:32])[CH3:30])[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 11370084HCID 11370084, compound

Product 1

HCID 11314674HCID 11314674, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.634 mL, 4.55 mmol) and cyclopropanecarbonyl chloride (0.248 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). The cloudy mixture was stirred for 2 hours at room temperature, 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, washed with dichloromethane and acetonitrile, and dried in a vacuum oven to provide 442 mg of N-{[4-Amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}cyclopropanecarboxamide as a hydrate, white crystals, mp 209-210° C.

Workup

  1. customwas partitioned between water (20 mL) and dichloromethane (30 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×30 mL)
  3. waitto stand overnight at room temperature
  4. customCrystals formed
  5. customwere isolated by filtration
  6. washwashed with dichloromethane and acetonitrile
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e6778e6790104c668999722726d003dd
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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