O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → (s)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-n-cyclopropylmethyl-2-[5-fluoro-2-methoxy-3-(2-oxo-piperidin-1-yl)-benzenesulfonylamino]-propionamide

HRID 76810

反応式

HRID 76810 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][C@H:13]([NH:17][S:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]4=[O:34])[C:22]=3[O:35][CH3:36])(=[O:20])=[O:19])[C:14](O)=[O:15])[CH:8]=2)=[CH:4][CH:3]=1.[CH:37]1(NC)[CH2:39][CH2:38]1.[B-](F)(F)(F)F.CCOC([C:52](C#N)=[N:53]OC(N(C)C)=[N+](C)C)=O>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][C@H:13]([NH:17][S:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]4=[O:34])[C:22]=3[O:35][CH3:36])(=[O:19])=[O:20])[C:14]([NH:53][CH2:52][CH:37]3[CH2:38][CH2:39]3)=[O:15])[CH:8]=2)=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11029756N-MethylcyclopropanamineHCID 66911181(s)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-2-[5-fluoro-2-methoxy-3-(2-oxo-piperidin-1-yl)-benzenesulfonylamino]-propionic acid

生成物 1

HCID 66911141(s)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-n-cyclopropylmethyl-2-[5-fluoro-2-methoxy-3-(2-oxo-piperidin-1-yl)-benzenesulfonylamino]-propionamide

反応条件

温度
50 °C

実験手順

Intermediate 17 (350 mg, 0.63 mmol) and cyclopropyl-methylamine (45 mg, 0.63 mmol) were coupled using the procedure described in example 1; 1.9), where only 25% conversion of starting materials was discovered. Heating to 50° C. did not lead to further conversion. Then TOTU (246 mg, 0.75 mmol) was added and after stirring for 1 h at RT conversion was completed. The mixture was purified by preparative HPLC. Yield after lyophilization: 162 mg, 43%, colorless, amorphous solid.

後処理

  1. customThe mixture was purified by preparative HPLC
  2. customYield after lyophilization

出典と根拠

ORDレコード
ord-84bb71aa225b41fe8bf187851ad05c28
出典データセット
uspto-grants-2014_09
特許番号
US08835653B2

関連ノート

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