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 357899노트

반응식

HRID 357899 반응식
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

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00a9233449794b94ad6798ba2f9097c6
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840909

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