Acetic Acid → HCID 86626308, compound

HRID 1097608

Reaction equation

HRID 1097608 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:18][O:19][C:20]([NH:22][C:23](=NC(OC)=O)OC)=[O:21].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:16][C:14]([CH3:17])([CH3:15])[CH2:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:23]1[NH:22][C:20](=[O:21])[O:19][CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 14986941HCID 14986941, compoundHCID 853487891,3-dimethoxycarbonyl-O-methylisourea

Product 1

HCID 86626308HCID 86626308, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol (1.0 g, 4.3 mmol), 1,3-dimethoxycarbonyl-O-methylisourea (prepared according to the general method of Viswanathan, N. Indian Patent No. 168,784, 1.64 g, 8.64 mmol), acetic acid (1.3 g, 22 mmol), and p-toluenesulfonic acid (0.82 g, 4.3 mmol) in methanol (20 mL) was heated at reflux for 16 hours. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform (100 mL). The solution was washed sequentially with water (100 mL), aqueous sodium carbonate (100 mL of 4% w/w), water (100 mL), and brine (100 mL) and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform) followed by recrystallization from acetonitrile to provide 0.64 g of methyl [1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate as a white solid, mp 225° C.

Workup

  1. customprepared
  2. temperatureat reflux for 16 hours
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform (100 mL)
  5. washThe solution was washed sequentially with water (100 mL), aqueous sodium carbonate (100 mL of 4% w/w), water (100 mL), and brine (100 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-472c74c0e8fe4f3da8c4ec9e479e1b28
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Linked notes

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