Triethylamine → ethyl 2-[1-[4-(4-chlorobenzamido)benzyl]-1H-indazol-3-yl]acetate

HRID 589369노트

반응식

HRID 589369 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:8]3)=[CH:22][CH:23]=2)=[O:37])=[CH:34][CH:33]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 89590263ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate

생성물 1

HCID 89590262ethyl 2-[1-[4-(4-chlorobenzamido)benzyl]-1H-indazol-3-yl]acetate수율 53.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

The crude ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate (about 0.663 mmol) obtained in the last step and triethylamine (1.0 mL) were dissolved in dichloromethane (15 mL). In an ice bath, a dichloromethane solution (10 mL) of 4-chlorobenzoyl chloride (117 mg, 0.669 mmol) was added dropwise slowly. Upon completion of the dropwise addition, it was reacted at room temperature for 16 hours. An aqueous solution of sodium bicarbonate was added to quench. It was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and filtered. The filtrate was rotate evaporated. The resulting residue was chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain a white solid 159 mg, at a total yield over two steps of reactions of 53.5%.

후처리

  1. additionUpon completion of the dropwise addition, it
  2. customwas reacted at room temperature for 16 hours
  3. customto quench
  4. extractionIt was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe resulting residue was chromatographed on a silica gel column (petroleum ether:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-718c27fc81c34ed4a27276ed7c61073d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233098B2

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