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

HRID 227969ノート

反応式

HRID 227969 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.[NH2:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1.Cl.CN(C)CCCN=C=NCC>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[CH2:6][CH2:5][C:4]([C:1]([NH:34][C:35]4[S:36][CH:37]=[CH:38][N:39]=4)=[O:2])([CH2:11][CH2:10]2)[CH2:9][CH2:8]3)[C@H:17]([C:22]#[N:23])[CH2:18]1

参加物

6

反応物 4

HCID 21552-AminothiazoleHCID 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 57756733(2S,4S)-4-fluoro-1-[[N-[4-[N-(thiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile収率 46.3%

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). To this solution, 2-aminothiazole (18.6 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53.4 mg) were added, and the mixture was stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure and the resulting residue was purified by preparative thin-layer chromatography (solvent:dichloromethane:methanol=9:1) to give (2S,4S)-4-fluoro-1-[[N-[4-[N-(thiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]pyrrolidine-2-carbonitrile (17.4 mg).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was purified by preparative thin-layer chromatography (solvent:dichloromethane:methanol=9:1)

出典と根拠

ORDレコード
ord-a9c2a9a933fb4fce81230d17c157eff5
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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