HCID 86724908, 화합물 → SUVN-D4010

HRID 1523733노트

반응식

HRID 1523733 반응식
[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]

참가 물질

4

반응물 2

HCID 86724908HCID 86724908, 화합물HCID 86724918HCID 86724918, 화합물

생성물 1

HCID 71508291SUVN-D4010수율 59.8%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

반응 조건

온도
0 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-d06447fddae34f92b84b2de8d1c9991e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079894B2

반응 노트

불러오는 중…