Dimethylformamide → (2S,4S)-N-[2-(4-Benzylpiperidin-1-yl)ethyl]-6-fluoro-2'5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide

HRID 373507

反応式

HRID 373507 の反応式
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.C1CCN2C(=NCCC2)CC1.CN(C)C=O.[F:33][C:34]1[CH:35]=[C:36]2[C@:43]3([C:47](=[O:48])[NH:46][C:45](=[O:49])[NH:44]3)[CH2:42][C@@H:41]([C:50](Cl)=[O:51])[O:40][C:37]2=[CH:38][CH:39]=1>>[CH2:10]([CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][NH:1][C:50]([C@@H:41]2[CH2:42][C@@:43]3([C:47](=[O:48])[NH:46][C:45](=[O:49])[NH:44]3)[C:36]3[C:37](=[CH:38][CH:39]=[C:34]([F:33])[CH:35]=3)[O:40]2)=[O:51])[CH2:9][CH2:8]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27798312-(4-Benzylpiperidin-1-yl)ethan-1-amineHCID 57210646(2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride

生成物 1

HCID 18648894(2S,4S)-N-[2-(4-Benzylpiperidin-1-yl)ethyl]-6-fluoro-2'5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide収率 50%

反応条件

温度
-30 °C

実験手順

A mixture of N-(2-aminoethyl)-4-benzylpiperidine (13.0 g, 59.6 mmol), 1,8-diazabicyclo[5,4,0]-7-undecene (10.9 g, 71.7 mmol) and N,N-dimethylformamide (90.0 ml, 1.16 mol) was chilled to -30° C. To the mixture was added over 30 minutes a solution of (2S, 4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride (Reference Example, 18.0 g, 60.3 mmol) in N,N-dimethylformamide (90.0 ml, 1.16 mol) and the mixture was stirred for 15 hours at temperature of 15°-25° C. After distilling off the solvent, the reaction mixture was chromatographed on silica gel, eluted with CH2Cl2 /MeOH (9/1) and evaporated in vacuo to dryness to give the desired compound (14.3 g, 50.0%) as colorless amorphous substance.

後処理

  1. distillationAfter distilling off the solvent
  2. customthe reaction mixture was chromatographed on silica gel
  3. washeluted with CH2Cl2 /MeOH (9/1)
  4. customevaporated in vacuo to dryness

出典と根拠

ORDレコード
ord-c6d5e1d3fcb54a83a48220d146ac0044
出典データセット
uspto-grants-1992_11
特許番号
US05164391

関連ノート

読み込み中…