4-(Trifluoromethyl)aniline → (2S,4S)-4-fluoro-1-[[N-[4-[N-(4-trifluoromethylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile

HRID 227975ノート

反応式

HRID 227975 の反応式
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)(O)=[O:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:46][C:47]([F:56])([F:55])[C:48]1[CH:54]=[CH:53][C:51]([NH2:52])=[CH:50][CH:49]=1.CN(C1C=CC=CN=1)C>CN(C)C=O>[F:21][C@@H:19]1[CH2:20][N:16]([C:14](=[O:15])[CH2:13][NH:12][C:7]23[CH2:10][CH2:11][C:4]([C:1]([NH:52][C:51]4[CH:53]=[CH:54][C:48]([C:47]([F:46])([F:55])[F:56])=[CH:49][CH:50]=4)=[O:2])([CH2:9][CH2:8]2)[CH2:5][CH2:6]3)[C@H:17]([C:22]#[N:23])[CH2:18]1

参加物

7

反応物 5

HCID 99644-(Trifluoromethyl)anilineHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

生成物 1

HCID 11259858(2S,4S)-4-fluoro-1-[[N-[4-[N-(4-trifluoromethylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(2S,4S)-1-[[N-(4-Carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (30.0 mg), along with 1-hydroxybenzotriazole, was dissolved in N,N-dimethylformamide (1.0 mL). While the solution was chilled in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53.4 mg) was added and the mixture was allowed to warm to room temperature and was stirred for 1 hour. Subsequently, 4-trifluoromethylaniline (23.0 μL) was added and the mixture was stirred for additional 12 hours, followed by addition of dimethylaminopyridine (11.3 mg) and stirring for additional 24 hours. The solvent was then evaporated under reduced pressure and the resulting residue was purified by preparative thin-layer chromatography (solvent:dichloromethane:methanol=4:1) to give (2S,4S)-4-fluoro-1-[[N-[4-[N-(4-trifluoromethylphenyl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile (10.1 mg).

後処理

  1. temperatureWhile the solution was chilled in an ice bath
  2. stirringthe mixture was stirred for additional 12 hours
  3. stirringstirring for additional 24 hours
  4. customThe solvent was then evaporated under reduced pressure
  5. customthe resulting residue was purified by preparative thin-layer chromatography (solvent:dichloromethane:methanol=4:1)

出典と根拠

ORDレコード
ord-8cff378499cc4339bc5ba944d6335f98
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

反応ノート

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