1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 9H-fluorene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177886

반응식

HRID 1177886 반응식
CCN(C(C)C)C(C)C.[CH:10]1[C:22]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[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.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][N:55]([C:58](=[O:69])[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]([F:68])([F:67])[F:66])[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[O:51]=[C:50]([N:52]1[CH2:53][CH2:54][N:55]([C:58](=[O:69])[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]([F:68])([F:67])[F:66])[CH2:56][CH2:57]1)[CH2:49][NH:48][C:23]([C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:21][C:22]=2[CH:10]=1)=[O:25]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3485919H-fluorene-2-carboxylic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

생성물 1

HCID 595596689H-fluorene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide수율 44%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (184 mg, 0.24 mL, 1.42 mmol) was added to a stirred solution of 9H-fluorene-2-carboxylic acid (100 mg, 0.47 mmol) in DMF (2 mL). HOBT (64 mg, 0.47 mmol) and EDCI (109 mg, 0.57 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (167 mg, 0.47 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated. The solid obtained was recrystallized from a mixture of ethyl acetate and hexane afford 105 mg (43.4%) of 9H-fluorene-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 98.25%. 1H NMR (DMSO-d6): δ 8.6 (m, 1H), 8.1 (s, 1H), 8.0-7.4 (m, 10H), 4.2 (bs, 2H), 4.0 (s, 2H), 3.8-3.4 (m, 6H), 3.2 (b, 2H).

후처리

  1. filtrationfiltered the solid
  2. customprecipitated
  3. customThe solid obtained
  4. customwas recrystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-50126fe048884e61ba55b4d479959fa1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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