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p-Toluenesulfonic acid → ethyl 2-(4-(4-chloro-2-methylphenyl)-1,3,7-trimethyl-4,6-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-6-yl)acetate

HRID 1748809
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HRID 1748809 반응식
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH3:8])=[N:3]1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[C:12]([CH3:18])[CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[SH:30][CH:31]([C:38](=O)[CH3:39])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C([O-])(O)=O.[Na+]>C(#N)C.C(Cl)Cl>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[S:30][CH:31]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:38]([CH3:39])=[N:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:8])[C:5]2=3)=[C:12]([CH3:18])[CH:11]=1
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8

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HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 27576584-Chloro-2-methylbenzaldehydeHCID 86724137Ethyl 3-mercapto-4-oxopentanoate

생성물 1

HCID 86724138ethyl 2-(4-(4-chloro-2-methylphenyl)-1,3,7-trimethyl-4,6-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-6-yl)acetate
수율 37.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
90 °C

실험 절차

To a solution of 1,3-dimethyl-1H-pyrazol-5-amine (0.58 g, 5.22 mmol, Oakwood Chemicals), 4-chloro-2-methylbenzaldehyde (0.81 g, 5.22 mmol, Ark Pharm) and p-TSA (0.10 g, 0.52 mmol) in acetonitrile (10.5 mL) was added ethyl 3-mercapto-4-oxopentanoate (1.74 g, 9.87 mmol) and stirred at about 90° C. for about 18 h. The reaction mixture was cooled to ambient temperature and saturated NaHCO3 (15 mL) and DCM (20 mL) were added. The organic layer was separated and the aqueous layer was back extracted using DCM (20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, EtOAc/heptane 100:0 to 0:50) to afford ethyl 2-(4-(4-chloro-2-methylphenyl)-1,3,7-trimethyl-4,6-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-6-yl)acetate (0.85 g, 1.97 mmol, 37%). LC-MS (Table 1, Method g) Rt=2.66, 2.63 min, m/z 406 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back extracted
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography (SiO2, EtOAc/heptane 100:0 to 0:50)

출처 및 근거

ORD 기록
ord-76e3b585e3414ca78b15c37c993a7ce5
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150592B2

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