2,2-Dimethylsuccinic anhydride → 4-(4-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid

HRID 1645346노트

반응식

HRID 1645346 반응식
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[S:20][C:19]4[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:18]=4[CH:17]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:26][C:27]1([CH3:34])[CH2:32][C:31](=[O:33])[O:30][C:28]1=[O:29]>C(Cl)Cl>[Cl:25][C:24]1[C:18]2[CH:17]=[C:16]([C:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([N:1]4[CH2:6][CH2:5][N:4]([C:31](=[O:33])[CH2:32][C:27]([CH3:34])([CH3:26])[C:28]([OH:30])=[O:29])[CH2:3][CH2:2]4)=[N:12][CH:11]=3)=[O:15])[S:20][C:19]=2[CH:21]=[CH:22][CH:23]=1

참가 물질

4

반응물 2

HCID 870672,2-Dimethylsuccinic anhydrideHCID 593651784-Chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

생성물 1

HCID 462078284-(4-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid수율 89.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide (50 mg, 0.13 mmol), CH2Cl2 (5 mL), and TEA (40 mg, 0.39 mmol) was stirred at room temperature. 2,2-Dimethylsuccinic anhydride (36 mg, 0.28 mmol) was added slowly. The reaction was stirred at room temperature for 0.5 hr then concentrated and the residue was taken up into 50 mL of EtOAc and washed with 50 mL of saturated ammonium chloride, brine and dried over anhydrous sodium sulfate. The solvent was removed and the product was triturated with diethyl ether and hexanes followed by filtration, to afford the product 4-(4-{5-[(4-chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-2,2-dimethyl-4-oxo-butyric acid (58 mg, 89% yield). LCMS for C24H25ClN4O4S calcd. (m/e) 500, observed 499 (M−H).

후처리

  1. stirringThe reaction was stirred at room temperature for 0.5 hr
  2. concentrationthen concentrated
  3. washwashed with 50 mL of saturated ammonium chloride, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe product was triturated with diethyl ether and hexanes
  7. filtrationfollowed by filtration

출처 및 근거

ORD 기록
ord-851927c92ab04157a1b7523151f01bd0
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124766B2

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