Potassium Iodide → N-[[[(2,6-diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine

HRID 492295

반응식

HRID 492295 반응식
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].[CH2:18]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]2[N:41]([C:42]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:40]=[N:39][N:38]=2)=[CH:27][CH:26]=1)[CH2:19][CH2:20][CH2:21][CH3:22].[I-].[K+].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH:15]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[C:6]=1[NH:5][C:3]([CH2:2][N:23]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]2[N:41]([C:42]([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:40]=[N:39][N:38]=2)=[CH:27][CH:26]=1)=[O:4])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 23637742-Chloro-N-(2,6-diisopropylphenyl)acetamideHCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine

생성물 1

HCID 68853185N-[[[(2,6-diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine수율 33%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

N-(Chloroacetyl)-2,6-diisopropylaniline (196.3 mg), N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (430.0 mg), potassium iodide (70 mg) and triethylamine (0.6 g) were suspended in dimethylformamide (3 mL). The resulting mixture was heated to about 80° C., and then stirred at that temperature. Three hours later, the reaction mixture was cooled, ethyl acetate (30 mL) was added, and the mixture was washed four times with brine (50 mL, each). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane/ethyl acetate) to afford N-[[[(2,6-diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (196.4 mg). Yield: 33%.

후처리

  1. temperatureThree hours later, the reaction mixture was cooled
  2. washthe mixture was washed four times with brine (50 mL
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8c9e5fa1e80247efa0c1083a5993c353
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531576B2

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