Acetic Acid → HCID 86626308, 화합물

HRID 1097608

반응식

HRID 1097608 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 86626308HCID 86626308, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-472c74c0e8fe4f3da8c4ec9e479e1b28
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143270B2

연결된 노트

불러오는 중…