Sodium Carbonate → N-[3'-(Acetylamino)-1,1'-biphenyl-4-yl]-2-(1-azabicyclo[2.2.2]oct-3-yl)acetamide Hydrochloride

HRID 722187노트

반응식

HRID 722187 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[ClH:20].[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[CH:23]([CH2:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=1)=[O:31])[CH2:22]2>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[ClH:20].[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:36]2[CH:35]=[CH:34][C:33]([NH:32][C:30](=[O:31])[CH2:29][CH:23]3[CH:24]4[CH2:25][CH2:26][N:21]([CH2:28][CH2:27]4)[CH2:22]3)=[CH:38][CH:37]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 218834482-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide Hydrochloride

생성물 1

HCID 21883474N-[3'-(Acetylamino)-1,1'-biphenyl-4-yl]-2-(1-azabicyclo[2.2.2]oct-3-yl)acetamide Hydrochloride

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

43.8 mg (0.24 mmol) of 3-(acetamido)phenylboronic acid, 0.33 ml (0.66 mmol) of 2M aqueous sodium carbonate solution and 8.1 mg (0.01 mmol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride are added to a solution of 80 mg (0.22 mmol) of 2-(1-azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide hydrochloride in 1.5 ml of DMF. The reaction mixture is stirred at 80° C. for 0.14 h, cooled, filtered through kieselguhr and then purified by preparative HPLC. The product fractions are concentrated, taken up in methanol, mixed with 4M HCl in dioxane and again concentrated. Drying under high vacuum results in 23 mg (20% of theory) of the title compound.

후처리

  1. temperaturecooled
  2. filtrationfiltered through kieselguhr
  3. custompurified by preparative HPLC
  4. concentrationThe product fractions are concentrated
  5. additionmixed with 4M HCl in dioxane
  6. concentrationagain concentrated
  7. customDrying under high vacuum

출처 및 근거

ORD 기록
ord-a6f60b2052a14ef5a9001db55abf9616
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138410B2

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