Hydrochloric Acid → 2-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-7,7-dimethyl-4,6,7,8-tetrahydroquinazolin-5(1H)-one

HRID 1929537

反応式

HRID 1929537 の反応式
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([NH2:10])=[NH:9])[CH:3]=1.[Cl:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.[CH3:21][C:22]1([CH3:30])[CH2:27][C:26](=[O:28])[CH2:25][C:24](=O)[CH2:23]1.C([O-])(=O)C.[Na+].Cl>C(O)C.O.C(OCC)(=O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:10][C:24]3[CH2:23][C:22]([CH3:30])([CH3:21])[CH2:27][C:26](=[O:28])[C:25]=3[CH:14]([C:13]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=3[Cl:11])[N:9]=2)[CH:3]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 31358DimedoneHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 202042Nicotinamidine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 250302952-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-7,7-dimethyl-4,6,7,8-tetrahydroquinazolin-5(1H)-one収率 26%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Pyridinecarboxamidine hydrochloride (Schaefer F. C., Peters G. A., et al. J. Org. Chem.; 1961; 26(2); 412-418.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 5,5-dimethyl-1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under refluxing for 18 hr, condensed, and ethyl acetate and water and 1N HCl were added to separate the layers. The water layer was adjusted with concentrated NaOH solution until the pH to be basic, then ethyl acetate was added and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate and separated by column chromatography to obtain a yellow solid of 0.22 g (yield 26%); mp 186-187° C. 1H-NMR (400 MHz, CDCl3) δ 1.15 (3H, s, CH3); 1.16 (3H, s, CH3); 2.31 (2H, s, CH2); 2.53-2.69 (2H, m, CH2); 6.07 (1H, s, CH); 6.94-6.96 (1H, m, ArH); 7.14-7.17 (1H, m, ArH); 7.23-7.26 (1H, m, ArH); 7.34-7.38 (1H, m, ArH) 8.07-8.09 (1H, m, ArH); 8.69-8.71 (1H, m, ArH); 8.89 (1H, m, ArH). MS (EI) 383.1 (M+).

後処理

  1. temperatureunder refluxing for 18 hr
  2. additionwere added
  3. customto separate the layers
  4. additionethyl acetate was added
  5. extractionextracted twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. customseparated by column chromatography
  8. customto obtain a yellow solid of 0.22 g (yield 26%)

出典と根拠

ORDレコード
ord-f0135dcc23d648ad9493a2fc9e0c3f90
出典データセット
uspto-grants-2012_05
特許番号
US08188091B2

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