1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44218283、化合物

HRID 46006ノート

反応式

HRID 46006 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20](O)=[O:21])[CH:13]1[CH2:15][CH2:14]1)(=[O:11])=[O:10].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH:55]1([N:58]2[CH2:63][CH2:62][N:61]([C:64]3([CH2:70][NH:71][C:72](=[O:79])[C:73]4[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=4)[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]3)[CH2:60][CH2:59]2)[CH2:57][CH2:56]1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20]([N:67]1[CH2:66][CH2:65][C:64]([CH2:70][NH:71][C:72](=[O:79])[C:73]2[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=2)([N:61]2[CH2:60][CH2:59][N:58]([CH:55]3[CH2:56][CH2:57]3)[CH2:63][CH2:62]2)[CH2:69][CH2:68]1)=[O:21])[CH:13]1[CH2:14][CH2:15]1)(=[O:10])=[O:11]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57453429HCID 57453429、化合物HCID 57916235HCID 57916235、化合物

生成物 1

HCID 44218283HCID 44218283、化合物収率 55%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

To a solution of 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)-ethoxy)acetic acid AC8 (0.225 mmol) in dichloromethane (10 ml/mmol) was added diisopropyl ethylamine (4 equiv.) at 0° C. followed by the addition of HOBT (1.0 equiv.) and EDCI (1.5 equiv.). The resulting solution was stirred at 25° C. for 15 min. It was again cooled to 0° C. and a solution of N-((4-(4-cyclopropyl-piperazin-1-yl)piperidin-4-yl)methyl)isonicotinamide dihydrochloride AM12 (1.2 equiv.) in DMF (2 ml) was added. The reaction mixture was stirred for 16 h at 25° C. The mixture was diluted with dichloromethane, washed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give the crude product which was purified by column chromatography. Yield: 55%. MS, Rt=2.8 min, m/z=673.4 [MH]+.

後処理

  1. temperatureIt was again cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 16 h at 25° C
  3. washwashed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-13b1eab9be1543a69f52f40536d97ad1
出典データセット
uspto-grants-2013_09
特許番号
US08541573B2

反応ノート

読み込み中…