1-Hydroxybenzotriazole → HCID 44235271、化合物

HRID 1093572ノート

反応式

HRID 1093572 の反応式
[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

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591525HCID 66591525、化合物

生成物 1

HCID 44235271HCID 44235271、化合物収率 24.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e9325b73234c48c7a61f11b7354e2dd7
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

読み込み中…