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

HRID 357898ノート

反応式

HRID 357898 の反応式
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

参加物

9

反応物 5

HCID 25517Ammonium ChlorideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 18522661Acetone cardice2 回HCID 221038291-(2-Phenylethyl)-3-amino-4-ethoxycarbonylpyrazoleHCID 86604122LDA cyclohexane

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒3 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0b408c4b41044b658709c8de84c6b442
出典データセット
uspto-grants-1998_11
特許番号
US05840909

反応ノート

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