Benzylamine → N-benzyl-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

HRID 83599

반응식

HRID 83599 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH2:59]([NH2:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C(Cl)Cl.O>[CH2:59]([NH:66][C:24]([CH:21]1[CH2:22][CH2:23][N:18]([C:16]([C:8]2[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=3)[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)=[O:17])[CH2:19][CH2:20]1)=[O:25])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

참가 물질

8

반응물 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

생성물 1

HCID 57385296N-benzyl-1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (200 mg, 0.500 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (115 mg, 0.600 mmol), and 1-Hydroxybenzotriazole (81 mg, 0.600 mmol) were dissolved in 10.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (131 μL, 0.750 mmol) and benzylamine (82 μL, 0.750 mmol) were added. The reaction was allowed to stir overnight. The reaction was diluted with water and dichloromethane. The layers were separated and the organic layer was washed with water, saturated ammonium chloride, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified using 10 gram silica Biotage column, with the gradient 30% ethyl acetate: hexanes to 100% ethyl acetate. After purification, pure white solid was obtained. Yield: 105 mg (White solid)

후처리

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with water, saturated ammonium chloride, and saturated sodium chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified
  8. customAfter purification
  9. custompure white solid was obtained

출처 및 근거

ORD 기록
ord-4aba10c93b674f179a10c39861549cec
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846684B2

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