Ammonium Chloride → N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl) methyl]amine

HRID 357898노트

반응식

HRID 357898 반응식
C([N-]C(C)C)(C)C.[Li+].[CH2:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1([CH2:21][CH2:22][N:23]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25]([NH2:33])=[N:24]2)C=CC=CC=1.C(=O)=O.CC(C)=O.Br[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[C:55]2[N:59]([C:60]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[N:58]=[N:57][N:56]=2)=[CH:45][CH:44]=1.[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.C1COCC1.CN1CCCN(C)C1=O>[C:9]1([CH2:21][CH2:22][N:23]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25]([NH:33][CH2:42][C:43]3[CH:44]=[CH:45][C:46]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=4[C:55]4[N:59]([C:60]([C:73]5[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=5)([C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)[C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[N:58]=[N:57][N:56]=4)=[CH:47][CH:48]=3)=[N:24]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

9

반응물 5

HCID 25517Ammonium ChlorideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 18522661Acetone cardice2회HCID 221038291-(2-Phenylethyl)-3-amino-4-ethoxycarbonylpyrazoleHCID 86604122LDA cyclohexane

생성물 1

HCID 67637880N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl) methyl]amine

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매3회HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매HCID 21226206Ethyl acetate hexane용매

실험 절차

2.1 ml of 1.5M lithium diisopropylamide/cyclohexane solution were added to THF solution (35 ml) containing 363 mg of 1-(2-phenylethyl)-3-amino-4-ethoxycarbonylpyrazole and 0.40 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, while cooling with dry ice-acetone, and stirred at room temperature for 15 minutes. The mixture was again cooled with dry ice-acetone, and 10 ml of THF solution of 877 mg of 4-bromomethyl-2'-[N-triphenylmethyl-(1H-tetrazol-5-yl)]biphenyl were added thereto and stirred at room temperature for 5.5 hours. 10 ml of aqueous ammonium chloride solution was added to the reaction solution, THF was distilled off under reduced pressure, and the resultant was extracted with 50 ml of dichloromethane. The resulting extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (n-hexane-ethyl acetate=3:1→2:1) to obtain 234 mg of the intended compound as a pale yellow, amorphous solid.

후처리

  1. additionwere added
  2. stirringstirred at room temperature for 5.5 hours
  3. distillationwas distilled off under reduced pressure
  4. extractionthe resultant was extracted with 50 ml of dichloromethane
  5. extractionThe resulting extract
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained

출처 및 근거

ORD 기록
ord-0b408c4b41044b658709c8de84c6b442
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840909

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