1-Hydroxybenzotriazole → HCID 44235271, 화합물

HRID 1093572노트

반응식

HRID 1093572 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.FC(F)(F)C(O)=O.[Br:58][C:59]1[CH:71]=[CH:70][CH:69]=[CH:68][C:60]=1[O:61][CH:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1>CN(C=O)C.O>[Br:58][C:59]1[CH:71]=[CH:70][CH:69]=[CH:68][C:60]=1[O:61][CH:62]1[CH2:67][CH2:66][N:65]([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])[CH2:64][CH2:63]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 66591525HCID 66591525, 화합물

생성물 1

HCID 44235271HCID 44235271, 화합물수율 24.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.08278 g, 0.00032 mol) in DMF (2 mL) was added, DIPEA (0.104 g, 0.00081 mol), HOBt (0.0437 g, 0.00032 mol) and EDCI.HCl (0.0619 g, 0.00032 mol) at ambient temperature. After 2 minutes 4-(2-bromo-phenoxy)-piperidine trifluoroacetate (0.1 g, 0.00027 mol) was added and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by preparative HPLC [(column-Zorbax XDB C18-21.2×150 mm, mobile phase-0.1% TFA in water (A)/acetonitrile (B), gradient: (Time): (% B)-0:50; 2:50; 5:80)]) to afford 0.033 g (22%) of biphenyl-4-carboxylic acid {2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 493.1 (M+1)+, 98.35%, 1H NMR (DMSO-d6): δ 8.65 (t, 1H), 8.0 (d, 2H), 7.8 (m, 4H), 7.6 (dd, 1H), 7.52 (t, 2H), 7.4 (m, 2H), 7.24 (m, 1H), 6.95 (m, 1H), 4.8 (m, 1H), 4.3 (m, 2H), 3.7 (m, 2H), 3.55 (m, 2H), 1.9 (m, 2H), 1.7 (m, 2H).

후처리

  1. customat ambient temperature
  2. extractionthe product was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by preparative HPLC [(column-Zorbax XDB C18-21.2×150 mm, mobile phase-0.1% TFA in water (A)/acetonitrile (B)

출처 및 근거

ORD 기록
ord-e9325b73234c48c7a61f11b7354e2dd7
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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