Hydrochloric Acid → HCID 178511147, 화합물

HRID 1935723노트

반응식

HRID 1935723 반응식
[Cl-].[Mg+2].[Cl-].[C:4]([CH2:6][C:7]([OH:9])=O)#[N:5].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:22]1([CH2:28][CH2:29][C:30]2[NH:31][C:32]3[C:38](C(O)=O)=[CH:37][CH:36]=[CH:35][C:33]=3[N:34]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.C(#N)C.C(N(CC)CC)C>[C:22]1([CH2:28][CH2:29][C:30]2[NH:34][C:33]3[C:35]([C:7](=[O:9])[CH2:6][C:4]#[N:5])=[CH:36][CH:37]=[CH:38][C:32]=3[N:31]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

10

반응물 6

HCID 313Hydrochloric AcidHCID 9740Cyanoacetic acid2회HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 5360315Magnesium ChlorideHCID 178524248HCID 178524248, 화합물

생성물 1

HCID 178511147HCID 178511147, 화합물수율 47.4%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

Triethylamine (5.2 mL) and magnesium chloride (4.3 g) were added to dry acetonitrile (30 mL) solution of cyanoacetic acid (1.6 g), and the mixture was vigorously stirred at room temperature for 23 hours under an atmosphere of argon. Next, a catalytically effective amount of N,N-dimethylaminopyridine and 1,1′-carbonyldiimidazole (1.34 g) were added to anhydrous tetrahydrofuran (20 mL) suspension of 2-(2-phenylethyl)benzimidazole-4-carboxylic acid (2.0 g) obtained in Reference Example 3, and the mixture was stirred for 2.5 hours under an atmosphere of argon. The reaction solution was added to the previously prepared cyanoacetic acid suspension of magnesium salt while cooling in an ice bath, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ice water (30 mL) and, at the same temperature, adjusted to pH 1 with 4 N hydrochloric acid. At the same temperature, this was adjusted to pH 9 with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) and the desired fraction was concentrated to obtain the title compound as colorless crystal (1.03 g).

후처리

  1. customobtained in Reference Example 3
  2. stirringthe mixture was stirred for 2.5 hours under an atmosphere of argon
  3. temperaturewhile cooling in an ice bath
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)
  10. concentrationthe desired fraction was concentrated

출처 및 근거

ORD 기록
ord-90c061a4fdee4d1091e23cfa1d9bcf99
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06387938B1

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