3-Aminopyridine → HCID 44235737, 화합물

HRID 1093884노트

반응식

HRID 1093884 반응식
CC[N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]2[CH:41]=[C:40]([C:42]([NH:44][CH2:45][C:46]([OH:48])=O)=[O:43])[N:39]=[N:38]2)[CH:32]=1.NC1C=NC=CC=1.FC(F)(F)C(O)=O.[F:63][C:64]([F:79])([F:78])[C:65]1[CH:77]=[CH:76][CH:75]=[CH:74][C:66]=1[O:67][CH:68]1CCNCC1.[Pb].O>CN(C=O)C>[O:48]=[C:46]([N:3]1[CH2:4][CH2:6][CH:68]([O:67][C:66]2[CH:74]=[CH:75][CH:76]=[CH:77][C:65]=2[C:64]([F:63])([F:78])[F:79])[CH2:9][CH2:7]1)[CH2:45][NH:44][C:42]([C:40]1[N:39]=[N:38][N:37]([C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)[CH:41]=1)=[O:43]

참가 물질

9

반응물 7

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1800858912168-64-8HCID 66592012[(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acidHCID 866346354-(2-Trifluoromethyl-phenoxy)-piperidine trifluoracetate

생성물 1

HCID 44235737HCID 44235737, 화합물수율 15.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DIPEA (156.8 mg, 1.5 mmol) followed by HOBt (53 mg, 0.29 mmol) and EDCI (75 mg, 0.39 mmol) were added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) (75 g, 0.3 mmol) in DMF (4 mL). After 2 minutes of stirring, 4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroacetate (85 mg, 0.3 mmol) was added and the resulting mixture was stirred at room temperature overnight. Addition of cold water lead to the formation of a precipitate which was collected and purified by preparative HPLC to afford 24 mg (15.6% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 475, 99.07%. 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.2 (d, 1H), 8.75 (m, 1H), 8.5 (t, 1H), 8.4 (m, 1H), 7.7-7.6 (m, 3H), 7.4-7.35 (d, 1H), 7.1 (t, 1H), 5.0 (q, 1H), 4.25 (d, 2H), 3.7-3.5 (m, 4H), 2.0-1.8 (m, 2H), 1.8-1.5 (m, 2H).

후처리

  1. customprepared by the method
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customwas collected
  4. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-a3f9de50751244ad8a409151de3a1464
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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