Acetic Acid → HCID 86626310, compound

HRID 1097611

Reaction equation

HRID 1097611 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].[CH3:17][O:18][C:19]([NH:21][C:22](=NC(OC)=O)OC)=[O:20].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][CH:2]([CH3:16])[CH2:3][N:4]1[C:5]2[C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=[C:22]1[NH:21][C:19](=[O:20])[O:18][CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 53699038N4-Isobutyl-1,5-naphthyridine-3,4-diamineHCID 853487891,3-dimethoxycarbonyl-O-methylisourea

Product 1

HCID 86626310HCID 86626310, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine (Gerster et al, U.S. Pat. No. 6,194,425, Example 30 Part A, 4.10 g, 19.0 mmol), 1,3-dimethoxycarbonyl-O-methylisourea (7.21 g, 37.9 mmol), acetic acid (5.69 g, 94.8 mmol), and p-toluenesulfonic acid (3.60 g, 19.0 mmol) in methanol (50 mL) was heated at reflux for 16 hours. The volatiles were removed under reduced pressure, and the residue was dissolved in chloroform (150 mL). The solution was washed sequentially with water (150 mL), aqueous sodium carbonate (150 mL of 4% w/w), water (150 mL), and brine (150 mL) and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 20% CMA in chloroform) followed by recrystallization from acetonitrile to provide 1.78 g of methyl [1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]carbamate as a white solid, mp 195-197° C.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (150 mL)
  4. washThe solution was washed sequentially with water (150 mL), aqueous sodium carbonate (150 mL of 4% w/w), water (150 mL), and brine (150 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 20% CMA in chloroform)
  7. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-6678059f397a435994898fa220c42068
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Linked notes

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