HCID 86724908、化合物 → SUVN-D4010

HRID 1523733ノート

反応式

HRID 1523733 の反応式
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:15][NH2:16])=[O:14])=[N:5]1)([CH3:3])[CH3:2].Cl.[CH3:18][O:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29](O)=O)[CH2:25][CH2:24]1>P(Cl)(Cl)(Cl)=O>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[O:14][C:29]([CH:26]3[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][CH2:20][O:19][CH3:18])[CH2:28][CH2:27]3)=[N:16][N:15]=2)=[N:5]1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 86724908HCID 86724908、化合物HCID 86724918HCID 86724918、化合物

生成物 1

HCID 71508291SUVN-D4010収率 59.8%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
0 °C

実験手順

To the mixture of 1-isopropyl-1H-indazole-3-carboxylic acid hydrazide (15.0 grams, 68.8 mmol) and 1-(3-Methoxy propyl)-piperidine-4-carboxylic acid hydrochloride (20.9 grams, 88.2 mmol, obtained in preparation 7) cooled at 0° C. was added phosphoryl chloride (130 mL). The reaction temperature was gradually raised to 100° C. and stirred was 2 hours. Upon completion of the reaction, it was cooled to 0° C. and triturated with hexanes (3×250 mL). The crude product was basified with aqueous sodium hydroxide solution and extracted with 5% methanol in dichloromethane. The combined organic layer was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 1-isopropyl-3-{5-[1-(3-methoxy propyl)piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-1H-indazole (15.78 grams)

後処理

  1. temperatureThe reaction temperature was gradually raised to 100° C.
  2. customUpon completion of the reaction, it
  3. temperaturewas cooled to 0° C.
  4. customtriturated with hexanes (3×250 mL)
  5. extractionextracted with 5% methanol in dichloromethane
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d06447fddae34f92b84b2de8d1c9991e
出典データセット
uspto-grants-2015_07
特許番号
US09079894B2

反応ノート

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