1-Hydroxybenzotriazole → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-2-yl)ethyl)piperidine-4-carboxamide

HRID 83618

반응식

HRID 83618 반응식
Cl.C(N=C=NCCCN(C)C)C.N1(O)C2C=CC=CC=2N=N1.[Cl:23][C:24]1[CH:50]=[CH:49][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([OH:48])=O)[CH2:42][CH2:41]2)=[O:39])=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C.[N:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[CH2:66][CH2:67][NH2:68]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:23][C:24]1[CH:50]=[CH:49][C:27]([CH2:28][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[C:30]2[C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]([NH:68][CH2:67][CH2:66][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][N:60]=3)=[O:48])[CH2:42][CH2:41]2)=[O:39])=[CH:26][CH:25]=1

참가 물질

9

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

생성물 1

HCID 665712761-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-2-yl)ethyl)piperidine-4-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (235 mg, 1.228 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (166 mg, 1.228 mmol), and 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (390 mg, 0.982 mmol) were dissolved in 4.0 mL of DCM. The reaction was stirred for ten minutes before adding N-ethyl-N-isopropylpropan-2-amine (0.214 ml, 1.228 mmol) and 2-(pyridin-2-yl)ethanamine (100 mg, 0.819 mmol) as a 1.0 mL DCM solution. The reaction was stirred overnight at room temperature. It was diluted with water and ethyl acetate. The organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated with ether and ethyl acetate and filtered to obtain white solid as a product. 1H-NMR (400 MHz, DMSO-d6) 8.46, 7.84, 7.66, 7.60, 7.51, 7.37-7.27, 7.24-7.14, 7.12-7.03, 6.69, 5.46, 4.58-3.75, 3.37, 3.12-2.67, 2.34-2.25, 1.59, 1.33

후처리

  1. stirringThe reaction was stirred overnight at room temperature
  2. washThe organic phase 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 crude material was triturated with ether and ethyl acetate
  7. filtrationfiltered
  8. customto obtain white solid as a product

출처 및 근거

ORD 기록
ord-ca1b81ceb127419fb23845b8dcf45c21
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846684B2

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