Potassium Carbonate → N-(2-{7-[(2S)-3-(4-Cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl}ethyl)-1-phenylmethanesulfonamide

HRID 1992398ノート

反応式

HRID 1992398 の反応式
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:11][CH:10]2[O:12][CH:6]([CH2:7][N:8]([CH2:13][C@H:14]([OH:25])[CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH2:9]2)[CH2:5]1.[C:26]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(N(CC)CC)C.C(#N)C>[C:21]([C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C@@H:14]([OH:25])[CH2:13][N:8]2[CH2:9][CH:10]3[O:12][CH:6]([CH2:5][N:4]([CH2:3][CH2:2][NH:1][S:33]([CH2:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:35])=[O:34])[CH2:11]3)[CH2:7]2)=[CH:24][CH:23]=1)#[N:22]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 685227854-{(2S)-3-[7-(2-Aminoethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile

生成物 1

HCID 11677749N-(2-{7-[(2S)-3-(4-Cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl}ethyl)-1-phenylmethanesulfonamide収率 72%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回

実験手順

4-{(2S)-3-[7-(2-Aminoethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile (0.096 g, 0.28 mmol; see step Preparation A above) was dissolved in a 1:2 ratio of DCM:acetonitrile (3 mL). Triethylamine (0.17 g, 1.68 mmol) was added, followed by phenylmethanesulfonyl chloride (0.068 g, 0.36 mmol). The mixture was stirred at room temperature overnight with K2CO3 (0.38 g, 2.77 mmol) to ensure that the free base of triethylamine was in the reaction mixture. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. Purification by preparative HPLC gave 0.1 g (72%) of the title compound.

後処理

  1. customstep Preparation A above)
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customPurification by preparative HPLC

出典と根拠

ORDレコード
ord-3d2dee7074094c1bae4eecfbea76a7fc
出典データセット
uspto-grants-2010_01
特許番号
US07648985B2

反応ノート

読み込み中…