1-Hydroxybenzotriazole → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-((1-methyl-1H-pyrazol-3-yl)methyl)piperidine-4-carboxamide

HRID 83628노트

반응식

HRID 83628 반응식
Cl.C(N=C=NCCCN(C)C)C.[Cl:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[C:20]2[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([C:36](O)=[O:37])[CH2:32][CH2:31]2)=[O:29])=[CH:16][CH:15]=1.N1(O)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[CH3:60][N:61]1[CH:65]=[CH:64][C:63]([CH2:66][NH2:67])=[N:62]1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:13][C:14]1[CH:40]=[CH:39][C:17]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[C:20]2[C:28]([N:30]2[CH2:31][CH2:32][CH:33]([C:36]([NH:67][CH2:66][C:63]3[CH:64]=[CH:65][N:61]([CH3:60])[N:62]=3)=[O:37])[CH2:34][CH2:35]2)=[O:29])=[CH:16][CH:15]=1

참가 물질

9

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7019419(1-Methylpyrazol-3-yl)methanamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

생성물 1

HCID 665713351-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-((1-methyl-1H-pyrazol-3-yl)methyl)piperidine-4-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (259 mg, 1.350 mmol), 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (428 mg, 1.080 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (182 mg, 1.350 mmol) were dissolved in 4.0 mL of DCM. The reaction was stirred at room temperature for ten minutes before Hunig's Base (0.236 ml, 1.350 mmol) and (1-methyl-1H-pyrazol-3-yl)methanamine (100 mg, 0.900 mmol) as a 1.0 mL DCM solution was added. The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The resulting material was triturated with ethyl acetate to obtain white solid as the product. 1H-NMR (400 MHz, DMSO-d6) 8.18, 7.66-7.51, 7.35, 7.22, 7.12, 6.73, 6.05, 5.49, 4.40, 4.18, 3.96, 3.77, 2.93, 2.41, 1.69, 1.44

후처리

  1. additionwas added
  2. washThe organic layer was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting material was triturated with ethyl acetate
  7. customto obtain white solid as the product

출처 및 근거

ORD 기록
ord-1a9f9eb6fb2849dc891c2361a2c2c9a7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846684B2

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