1-Hydroxybenzotriazole → HCID 44235274, 화합물

HRID 1093578노트

반응식

HRID 1093578 반응식
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[N:59]([CH3:66])[CH:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1>CN(C=O)C.O>[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[N:59]([CH3:66])[CH:60]1[CH2:65][CH2:64][N:63]([C:11](=[O:13])[CH2:10][NH:9][C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:6][CH:5]=2)=[O:8])[CH2:62][CH2:61]1

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591780HCID 66591780, 화합물

생성물 1

HCID 44235274HCID 44235274, 화합물수율 36.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.1 g, 0.00039 mol) in DMF (2 mL), was added DIPEA (0.2025 g, 0.00156 mol), HOBt (0.053 g, 0.00039 mol) and EDCI.HCl (0.0901 g, 0.00047 mol) at ambient temperature. After 2 minutes (2-bromo-phenyl)-methyl-piperidin-4-yl-amine hydrochloride (0.119 g, 0.00039 mol) was added and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with cold water, and the resulting precipitate was isolated by filtration. Purification by preparative TLC using 30% ethyl acetate in hexane afforded 0.072 g (36%) of biphenyl-4-carboxylic acid (2-{4-[(2-bromo-phenyl)-methyl-amino]-piperidin-1-yl}-2-oxo-ethyl)-amide. LCMS: 506.1 (M+1)+, 97.07%, 1H NMR (DMSO-d6): δ 8.6 (t, 1H), 8.0 (d, 2H), 7.8 (d, 2H), 7.75 (m, 4H), 7.6-7.25 (m, 6H), 7.0 (t, 1H), 4.4 (m, 1H), 4.2 (m, 1H), 3.9 (m, 1H), 3.05 (m, 1H), 2.7 (m, 1H), 2.6 (s, 3H), 1.8-1.5 (m, 4H).

후처리

  1. customthe resulting precipitate was isolated by filtration
  2. customPurification by preparative TLC

출처 및 근거

ORD 기록
ord-758665fc541c4d1dac5b47cfeb9d3bcf
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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