1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Dibenzofuran-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177881ノート

反応式

HRID 1177881 の反応式
CCN(C(C)C)C(C)C.[CH:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[CH:13]=[CH:12][C:11]=1[C:23]([OH:25])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:54][CH2:55][C:56]([N:58]1[CH2:63][CH2:62][N:61]([C:64](=[O:75])[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=2[C:71]([F:74])([F:73])[F:72])[CH2:60][CH2:59]1)=[O:57]>CN(C=O)C.O>[O:57]=[C:56]([N:58]1[CH2:59][CH2:60][N:61]([C:64](=[O:75])[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][C:66]=2[C:71]([F:74])([F:73])[F:72])[CH2:62][CH2:63]1)[CH2:55][NH:54][C:23]([C:11]1[CH:12]=[CH:13][C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[C:18]=2[CH:10]=1)=[O:25]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4174048-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-carboxylic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

生成物 1

HCID 59559637Dibenzofuran-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide収率 33.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (137 mg, 0.18 mL, 1.06 mmol) was added to a stirred solution of dibenzofuran-2-carboxylic acid (75 mg, 0.35 mmol) in DMF (3 mL). HOBT (47.8 mg, 0.35 mmol) and EDCI (81.3 mg, 0.42 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (166 mg, 0.38 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated to afford 60 mg (33.3%) of dibenzofuran-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.09%. 1H NMR (DMSO-d6): δ 8.7 (bs, 2H), 8.2 (d, 1H), 8.06 (d, 1H), 7.9-7.55 (m, 7H), 7.55 (t, 1H), 4.41-4.3 (bs, 2H), 3.8-3.6 (bs, 4H), 3.5-3.4 (bs, 2H), 3.2-3.0 (bs, 2H).

後処理

  1. filtrationfiltered the solid
  2. customprecipitated

出典と根拠

ORDレコード
ord-da3c82b78e184cd6859a7284c71df3ff
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

読み込み中…