Ammonium Chloride → N-[1-(2-phenylethyl)-4-ethoxycarbonyl-5-bromopyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

HRID 357899ノート

反応式

HRID 357899 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC.[C:17]1([CH2:23][CH2:24][N:25]2[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:27]([N:35]([CH2:73][CH2:74][CH3:75])[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]4[N:53]([C:54]([C:67]5[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=5)([C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[C:55]5[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=5)[N:52]=[N:51][N:50]=4)=[CH:39][CH:38]=3)=[N:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Br:76]C(F)(F)C(Br)(F)F.[Cl-].[NH4+]>C1COCC1.CN1CCCN(C)C1=O>[C:17]1([CH2:23][CH2:24][N:25]2[C:29]([Br:76])=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:27]([N:35]([CH2:73][CH2:74][CH3:75])[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]4[N:53]([C:54]([C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)([C:61]5[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=5)[C:55]5[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=5)[N:52]=[N:51][N:50]=4)=[CH:39][CH:38]=3)=[N:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 22103832N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamineHCID 86588928Lithium bis(trimethylsilyl)amide hexane

生成物 1

HCID 22103828N-[1-(2-phenylethyl)-4-ethoxycarbonyl-5-bromopyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

実験手順

1.52 ml of 1.0M lithium bis(trimethylsilyl)amide/hexane solution were added to THF solution (20 ml) containing 395 mg of N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine and 0.18 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, at room temperature, and then heated under reflux for 30 minutes. 0.60 ml of 1,2-dibromo-1,1,2,2-tetrafluoroethane was added thereto and heated under reflux for further 30 minutes. 10 ml of ammonium chloride were added to the reaction solution, THF was distilled off under reduced pressure, and the resultant was extracted with 150 ml of dichloromethane. The resulting extract was dried over magnesium sulfate and subjected to silica gel column chromatography (n-hexane-ethyl acetate=2:1) to obtain 363 mg of the intended compound as a pale red, amorphous solid.

後処理

  1. temperatureunder reflux for 30 minutes
  2. temperatureheated
  3. temperatureunder reflux for further 30 minutes
  4. distillationwas distilled off under reduced pressure
  5. extractionthe resultant was extracted with 150 ml of dichloromethane
  6. extractionThe resulting extract
  7. dry with materialwas dried over magnesium sulfate

出典と根拠

ORDレコード
ord-00a9233449794b94ad6798ba2f9097c6
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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