Hydrochloric Acid → [1-Phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone

HRID 2039858노트

반응식

HRID 2039858 반응식
[Br-].CC([Zn+])C1C=CC=CC=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.Cl.Cl.Cl.[C:32]1([N:38]2[C:46]3[C:41](=[N:42][CH:43]=[CH:44][CH:45]=3)[C:40]([C:47]([N:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)=[O:48])=[C:39]2[CH:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH3:56])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:32]1([N:38]2[C:46]3[C:41](=[N:42][CH:43]=[CH:44][CH:45]=3)[C:40]([C:47]([N:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)=[O:48])=[C:39]2[CH:55]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH3:56])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 66922091[1-phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochlorideHCID 178462437HCID 178462437, 화합물

생성물 1

HCID 56661689[1-Phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of the compound of example 1, step 5, (120 mg, 27 μmol), α-methylbenzylzinc bromide (820 μl, 408 μmol, 0.5 M in THF), tri(tert-butyl)phosphonium tetrafluoroborate (15.6 mg, 54 μmol) and bis(dibenzylideneacetone)palladium (15.6 mg, 27 μmol) in THF (5 ml) was stirred for 12 h at 80° C. The reaction mixture was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The intermediate was purified by preparative HPLC and reacted analogously as described in example 1, step 7. The obtained solid was dissolved in a small quantity of MOH, mixed with hydrochloric acid (0.1 M) and lyophilized overnight to give 20 mg of the title compound in the form of the [1-phenyl-2-(1-phenyl-ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]-piperazin-1-yl-methanone dihydrochloride.

후처리

  1. extractionextracted with EA
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe intermediate was purified by preparative HPLC
  6. customreacted analogously
  7. dissolutionThe obtained solid was dissolved in a small quantity of MOH

출처 및 근거

ORD 기록
ord-3070da145ed3418988131c2998c45f95
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580813B2

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