Potassium Carbonate → HCID 11522204、化合物

HRID 2217333ノート

反応式

HRID 2217333 の反応式
[S:1]1[C:5]2[CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[N:3]=[C:2]1[NH2:13].C(=O)([O-])[O-].[K+].[K+].[CH3:20][N:21]1[C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=[N:22]1>O1CCCC1>[S:1]1[C:5]2[CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[N:3]=[C:2]1[NH:13][C:26]([C:25]1[N:21]([CH3:20])[N:22]=[CH:23][CH:24]=1)=[O:27]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 31649321-methyl-1H-pyrazole-5-carbonyl chlorideHCID 131876678H-indeno[1,2-d][1,3]thiazol-2-amine

生成物 1

HCID 11522204HCID 11522204、化合物収率 30.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture 8H-Indeno[1,2-d]thiazol-2-ylamine 1b (Prepared in Example 1, Step 2, 320 mg; 1.70 mmol) and potassium carbonate (3.10 g; 22.4 mmol) in dry tetrahydrofuran (10 mL) under nitrogen was added 2-methyl-2H-pyrazole-3-carbonyl chloride (516 mg; 3.57 mmol). The slurry was then heated to reflux for 3 hr. The solvent was removed in vacuo, and the residue diluted with water and extracted with ethyl acetate. The organic layer was washed with 50 mL of 1N hydrochloric acid solution followed by brine solution and dried (sodium sulfate) filtered and concentrated in vacuo. The crude product was purified by trituration with diethyl ether to provide 155 mg of 2-Methyl-2H-pyrazole-3-carboxylic acid (8H-indeno[1,2-d]thiazol-2-yl)-amide 9. EI-HRMS m/e calcd for C15H12N4OS (M+) 296.0732, found 296.0731.

後処理

  1. temperatureThe slurry was then heated
  2. temperatureto reflux for 3 hr
  3. customThe solvent was removed in vacuo
  4. additionthe residue diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 50 mL of 1N hydrochloric acid solution
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by trituration with diethyl ether

出典と根拠

ORDレコード
ord-0e489f83f2ba420390f0c4c5c0621ea3
出典データセット
uspto-grants-2008_08
特許番号
US07407977B2

反応ノート

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