Triethylamine → 1-[3-(1-Methyl-1H-tetrazol-5-yl)-phenyl]-3-{1-[2-(4-trifluoromethylphenyl)-ethyl]-piperidin-3-ylmethyl}-urea

HRID 896527노트

반응식

HRID 896527 반응식
Cl.[CH3:2][N:3]1[C:7]([C:8]2[CH:9]=[C:10]([NH:14][C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)=[O:16])[CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[N:4]1.[F:25][C:26]([F:47])([F:46])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:29][CH:28]=1.C(N(CC)CC)C>C(#N)C>[CH3:2][N:3]1[C:7]([C:8]2[CH:9]=[C:10]([NH:14][C:15]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:34][CH2:33][C:30]4[CH:29]=[CH:28][C:27]([C:26]([F:25])([F:46])[F:47])=[CH:32][CH:31]=4)[CH2:20]3)=[O:16])[CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[N:4]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18411913HCID 18411913, 화합물HCID 223502531-[3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-piperidin-3-ylmethylurea hydrochloride

생성물 1

HCID 100741821-[3-(1-Methyl-1H-tetrazol-5-yl)-phenyl]-3-{1-[2-(4-trifluoromethylphenyl)-ethyl]-piperidin-3-ylmethyl}-urea수율 45%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-[3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-piperidin-3-ylmethylurea hydrochloride (50 mg, 142 μmol), toluene-4-sulfonic acid 2-(4-trifluoromethyl-phenyl)-ethyl ester (90% pure, 55 mg, 142 μmol), triethylamine (60 μL, 426 μmol) and acetonitrile (1.5 mL) was heated at reflux for 16.5 hours and cooled to room temperature. The mixture was concentrated, and the residue was purified by flash chromatography, eluting with 3% methanol in dichloromethane containing 0.3% aqueous ammonium hydroxide, to provide a white amorphous solid (30 mg, 45%). 1H NMR (300 MHz, CDCl3) δ8.26 (s, !H), 7.87 (d, J=8 Hz, 1H), 7.76 (s, 1H), 7.51 (d, J=8 Hz, 1H), 7.39 (t, J=8 Hz, 1H), 7.28 (d, J=8 Hz, 2H), 7.20 (d, J=8 Hz, 1H), 6.06 (bm, 1H), 4.15 (s, 3H), 3.23 (t, J=6 Hz, 2H), 3.03 (m, 1H), 2.86 (m, 2H), 2.61 (m, 2H), 2.1-1.5 (m, 7H), 1.05 (m, 1H). Mass spec (ES+) m/z 488.5 (M+H+, 100%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 16.5 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by flash chromatography
  5. washeluting with 3% methanol in dichloromethane containing 0.3% aqueous ammonium hydroxide

출처 및 근거

ORD 기록
ord-671c3ec367984e7ba27371941bcb3f56
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919356B2

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