Phosgene → 1H-indazol-3-yl 4-methylpiperidine-1-carboxylate

HRID 2427829노트

반응식

HRID 2427829 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([OH:10])=[N:2]1.[C:11](Cl)(Cl)=[O:12].[CH3:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C1COCC1.C1(C)C=CC=CC=1>[CH3:15][CH:16]1[CH2:21][CH2:20][N:19]([C:11]([O:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[O:12])[CH2:18][CH2:17]1

참가 물질

6

반응물 3

HCID 6371PhosgeneHCID 693814-MethylpiperidineHCID 81829Indazolinone

생성물 1

HCID 111845121H-indazol-3-yl 4-methylpiperidine-1-carboxylate

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

300 mg (2.24 mmol) of 1H-indazol-3-ol were dissolved in 25 ml of THF and cooled to −20° C.: 1.3 ml (2.46 mmol) of phosgene in toluene (20 percent) were added dropwise and the reaction mixture was stirred for 90 min, during which it warmed to room temperature. The reaction mixture was concentrated and evacuated once again with a few ml of toluene. The residue was dissolved in 15 ml of THF, 265 μl (2.2 mmol) of 4-methylpiperidine were added dropwise and the mixture was stirred at room temperature for 3 h, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 347 mg (60%), M+H+: 260.4.

후처리

  1. temperaturewarmed to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. stirringthe mixture was stirred at room temperature for 3 h
  4. concentrationconcentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

출처 및 근거

ORD 기록
ord-0cd060e9f7484cefafbef267f6f48a7d
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968719B2

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