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1-Hydroxybenzotriazole → HCID 44235961, 화합물

HRID 1093596
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HRID 1093596 반응식
[C:1]1([NH:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])=[CH:10][CH:9]=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:59][C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][C:61]=1[O:62][CH:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>CN(C=O)C.O>[Br:59][C:60]1[CH:72]=[CH:71][CH:70]=[CH:69][C:61]=1[O:62][CH:63]1[CH2:68][CH2:67][N:66]([C:16](=[O:18])[CH2:15][NH:14][C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:20][CH:19]=2)[CH2:65][CH2:64]1
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참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874498(4-Phenylamino-benzoylamino)-acetic acidHCID 66591525HCID 66591525, 화합물

생성물 1

HCID 44235961HCID 44235961, 화합물
수율 32.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of (4-phenylamino-benzoylamino)-acetic acid (0.087 g, 0.00032 mol) in DMF (5 mL) was added DIPEA (0.104 g, 0.00081 mol), HOBt (0.043 g, 0.00032 mol) and EDCI.HCl (0.061 g, 0.00032 mol) at ambient temperature. After 2 minutes 4-(2-bromo-phenoxy)-piperidine trifluoroacetate (0.1 g, 0.00027 mol) and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulfate. The organic layer was collected and concentrated under reduced pressure to afford 0.045 g (32%) of N-{2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LCMS: 508.12 (M+1)+, 96.85%, 1H NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 2H), 7.6 (dd, 1H), 7.3 (m, 4H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (q, 2H), 4.8 (m, 1H), 4.2 (t, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 2.0 (m, 2H), 1.7 (m, 2H).

후처리

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. customThe organic layer was collected
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-addbb51e0809430b8bf7fcfaa26f2d95
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129376B2

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