Benzoyl chloride → HCID 67074466, 화합물

HRID 336862노트

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HRID 336862 반응식
[C:1]([N:5]1[C:9]2=[N:10][C:11]([C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][C:36]=3[F:42])=[C:12]([C:33]#[N:34])[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[C:8]2[C:7]([CH3:43])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:51](Cl)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>ClCCl>[C:51]([O:41][C:38]1[CH:39]=[CH:40][C:35]([C:11]2[N:10]=[C:9]3[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[N:6]=[C:7]([CH3:43])[C:8]3=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]4)=[CH:18][CH:19]=3)[C:12]=2[C:33]#[N:34])=[C:36]([F:42])[CH:37]=1)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 136353000HCID 136353000, 화합물

생성물 1

HCID 67074466HCID 67074466, 화합물수율 98.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 0.33 g (0.56 mmol) of tert-butyl 4-(4-(1-tert-butyl-5-cyano-6-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate and 325 μL (0.24 g, 2.3 mmol) of triethylamine in 17 ml of anhydrous dichloromethane are added dropwise 78 μL (0.09 g, 0.67 mmol) of benzoyl chloride. The mixture is stirred at room temperature for 24 h. The mixture is diluted with dichloromethane and washed with water. The aqueous phase is then extracted with dichloromethane. The organic phases are combined, dried over sodium sulfate, and concentrated to give 0.38 g (quantitative) of tert-butyl 4-(4-(6-(4-(benzoyloxy)-2-fluorophenyl)-1-tert-butyl-5-cyano-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate which is used in the following step without purification.

후처리

  1. washwashed with water
  2. extractionThe aqueous phase is then extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-443caa5a05244d5891adeb3d1dd7ca7b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889711B2

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