1-Hydroxybenzotriazole → HCID 178523490, 화합물

HRID 1093603노트

반응식

HRID 1093603 반응식
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[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.FC(F)(F)C(O)=O.[Br:57][C:58]1[CH:70]=[CH:69][CH:68]=[CH:67][C:59]=1[O:60][CH:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>CN(C=O)C.O>[Br:57][C:58]1[CH:70]=[CH:69][CH:68]=[CH:67][C:59]=1[O:60][CH:61]1[CH2:66][CH2:65][N:64]([C:16](=[O:18])[CH2:15][NH:14][C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][N:10]=2)=[O:13])[CH2:63][CH2:62]1

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591525HCID 66591525, 화합물HCID 178525878HCID 178525878, 화합물

생성물 1

HCID 178523490HCID 178523490, 화합물수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.038 g, 0.000135 mol) in DMF (2 mL) was added DIPEA (0.0872 g, 0.00068 mol), HOBt (0.023 g, 0.00017 mol) and EDCI.HCl (0.0325 g, 0.00017 mol) at ambient temperature. After 2 minutes 4-(2-bromophenoxy)-piperidine trifluoroacetate (0.05 g, 0.0001349 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried to afford 0.044 g (68%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 483.1 (M+1)+, 99.71%, 1H NMR (DMSO-d6): δ 13.7 (s, 1H), 8.02 (s, 1H), 7.79 (d, 1H), 7.6 (m, 1H), 7.42 (m, 2H), 7.3 (m, 2H), 7.26 (d, 1H), 7.0 (s, 1H), 6.9 (t, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.4 (m, 4H), 1.7 (m, 2H), 1.6 (m, 2H).

후처리

  1. customThe resulting precipitate was isolated by filtration
  2. customdried

출처 및 근거

ORD 기록
ord-40beaae5e84d478f8341323f8ec8f622
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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