Acetic Acid → HCID 86626310, 화합물

HRID 1097611

반응식

HRID 1097611 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 86626310HCID 86626310, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6678059f397a435994898fa220c42068
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143270B2

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