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

HRID 1177881노트

반응식

HRID 1177881 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  1. filtrationfiltered the solid
  2. customprecipitated

출처 및 근거

ORD 기록
ord-da3c82b78e184cd6859a7284c71df3ff
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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