Ethyl chloroacetate → Ethyl 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660914노트

반응식

HRID 660914 반응식
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14]1[N:15]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:16](=[O:19])[NH:17][N:18]=1.Cl[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(#N)C>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14]1[N:15]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:16](=[O:19])[N:17]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:18]=1

참가 물질

5

반응물 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580116455-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 58011923Ethyl 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

570 mg (4.12 mmol) of potassium carbonate are added to a suspension of 560 mg (2.06 mmol) of 5-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 247A and 253 mg (2.06 mmol) of ethyl chloroacetate in 10 ml acetonitrile and heated for 4 hrs under reflux. For the workup, this is concentrated, and the residue taken up in water and extracted three times with ethyl acetate. The combined organic phases are concentrated, and the crude product remaining as the residue is purified by preparative HPLC [Method 12]. 705 mg (96% of theory) of the target compound are thus obtained.

후처리

  1. temperatureheated for 4 hrs
  2. temperatureunder reflux
  3. concentrationFor the workup, this is concentrated
  4. extractionextracted three times with ethyl acetate
  5. concentrationThe combined organic phases are concentrated
  6. customis purified by preparative HPLC [Method 12]
  7. custom705 mg (96% of theory) of the target compound are thus obtained

출처 및 근거

ORD 기록
ord-80f3279430664672af91d1fc59e39358
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084481B2

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