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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
ノート
印刷プレビュー

反応式

HRID 1748809 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 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
収率 37.7%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-76e3b585e3414ca78b15c37c993a7ce5
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150592B2

反応ノート

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