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

HRID 1929538

反応式

HRID 1929538 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.[C:21]1(=O)[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH2:22]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:21]3[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[C:22]=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 104341,3-CyclohexanedioneHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 202042Nicotinamidine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 250302972-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-4,6,7,8-tetrahydroquinazolin-5(1H)-one収率 27%

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, 1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under reflexing for 18 hr, condensed, to which ethyl acetate, water and 1N HCl were added and then the layers were separated. 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 0.21 g (yield 27%); 1H-NMR (400 MHz, CDCl3) δ 2.13-2.17 (2H, m, CH2); 2.43-2.51 (2H, m, CH2); 2.63-2.83 (2H, m, CH2); 6.06 (1H, s, CH); 7.15-7.22 (2H, m, ArH); 7.34-7.38 (1H, m, ArH); 8.07-8.09 (1H, m, ArH); 8.70-8.71 (1H, m, ArH); 8.89 (1H, m, ArH). MS (HREI) 355.0887 (M+).

後処理

  1. customcondensed
  2. customthe layers were separated
  3. additionethyl acetate was added
  4. extractionextracted twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. customseparated by column chromatography
  7. customto obtain a yellow solid of 0.21 g (yield 27%)

出典と根拠

ORDレコード
ord-c7f175dbfd0c43549c510f6913488306
出典データセット
uspto-grants-2012_05
特許番号
US08188091B2

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