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1-Hydroxybenzotriazole → Biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-amide

HRID 1093575
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HRID 1093575 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.Cl.[NH:53]1[CH2:58][CH2:57][CH:56]([NH:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])[CH2:55][CH2:54]1>CN(C=O)C.O>[O:13]=[C:11]([N:53]1[CH2:54][CH2:55][CH:56]([NH:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:67])([F:68])[F:69])[CH2:57][CH2:58]1)[CH2:10][NH:9][C:7]([C:4]1[CH:3]=[CH:2][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)=[O:8]
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참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591440Piperidin-4-yl-(2-trifluoromethyl-phenyl)-amine dihydrochloride

생성물 1

HCID 57874380
Biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-amide
수율 72.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.03219 g, 0.00012 mol) in DMF (1 mL), was added, DIPEA (0.065 g, 0.0005 mol), HOBt (0.017 g, 0.00012 mol) and EDCI.HCl (0.2689 g, 0.00013 mol) at ambient temperature. After 2 minutes piperidin-4-yl-(2-trifluoromethyl-phenyl)-amine dihydrochloride (0.04 g, 0.00012 mol) was 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. The solid was recrystallized from a mixture of ethyl acetate and hexane to afford 0.042 g (61%) of biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenylamino)-piperidin-1-yl]-ethyl}-amide. LCMS: 482.1 (M+1)+, 97.99%, 1H NMR (DMSO-d6): δ 8.6 (t, 1H), 8.0 (m, 2H), 7.78-7.5 (m, 4H), 7.6-7.4 (m, 5H), 7.0 (d, 1H), 6.7 (t, 1H), 4.7 (d, 1H), 4.3 (m, 1H), 4.2 (d, 2H), 4.0-3.7 (m, 2H), 3.2 (m, 2H), 2.8 (m, 2H), 2.0 (m, 3H), 1.6-1.2 (m, 4H).

후처리

  1. customat ambient temperature
  2. customthe resulting precipitate was isolated by filtration
  3. customThe solid was recrystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-5422131c74324721afce12f127f27672
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129376B2

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