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

HRID 722187ノート

反応式

HRID 722187 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a6f60b2052a14ef5a9001db55abf9616
出典データセット
uspto-grants-2006_11
特許番号
US07138410B2

反応ノート

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