Triethylamine → 1-((1R,2S)-2-(((3-(4-fluorophenyl)propyl)(methyl)amino)methyl)cyclohexyl)-3-(3-(1-methyl-1H-tetrazol-5-yl)phenyl)urea

HRID 1592328노트

반응식

HRID 1592328 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[NH2:20])[CH3:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.C1([O:34][C:35](=O)[NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]3[N:47]([CH3:48])[N:46]=[N:45][N:44]=3)[CH:38]=2)C=CC=CC=1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[NH:20][C:35]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]3[N:47]([CH3:48])[N:46]=[N:45][N:44]=3)[CH:38]=2)=[O:34])[CH3:12])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69426356(1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine

생성물 1

HCID 112369501-((1R,2S)-2-(((3-(4-fluorophenyl)propyl)(methyl)amino)methyl)cyclohexyl)-3-(3-(1-methyl-1H-tetrazol-5-yl)phenyl)urea수율 60.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of (1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine (72 mg, 259 μmol) in acetonitrile (2 mL) was treated with triethylamine (72 μL, 517 μmol) and [3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (76 mg, 259 μmol). The mixture was stirred at room temperature for 15.5 hours and then was concentrated under vacuum. The residue was dissolved in ethyl acetate, and the solution was washed sequentially with 1.0 M aqueous sodium hydroxide, water and saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 4% methanol in dichloromethane containing 0.4% aqueous ammonium hydroxide, to provide a white amorphous solid (75 mg, 60%).

후처리

  1. concentrationwas concentrated under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed sequentially with 1.0 M aqueous sodium hydroxide, water and saturated aqueous sodium chloride
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting with 4% methanol in dichloromethane containing 0.4% aqueous ammonium hydroxide

출처 및 근거

ORD 기록
ord-690b5b8d2d114d08b29bf7cd0069351d
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291744B2

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