1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58116841, Verbindung

HRID 38601

Reaktionsgleichung

Reaktionsgleichung von HRID 38601
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[N:8]1([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.[Cl:30][C:31]1[CH:32]=[C:33]([NH:38][C:39]2[C:40]3[C:47]4[CH2:48][CH2:49][NH:50][CH2:51][C:46]=4[S:45][C:41]=3[N:42]=[CH:43][N:44]=2)[CH:34]=[CH:35][C:36]=1[Cl:37].CCN=C=NCCCN(C)C>C(Cl)Cl.O>[Cl:30][C:31]1[CH:32]=[C:33]([NH:38][C:39]2[C:40]3[C:47]4[CH2:48][CH2:49][N:50]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:11]5[CH2:10][CH2:9][N:8]([C:14]([N:16]6[CH2:17][CH2:18][CH2:19][CH2:20]6)=[O:15])[CH2:13][CH2:12]5)[CH2:51][C:46]=4[S:45][C:41]=3[N:42]=[CH:43][N:44]=2)[CH:34]=[CH:35][C:36]=1[Cl:37]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531Diisopropylethylamine2×HCID 2760443Piperazin-1-yl-pyrrolidin-1-yl-methanoneHCID 64364114-Bromocrotonic acidHCID 58116912(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine

Produkt 1

HCID 58116841HCID 58116841, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(2E)-4-Bromobut-2-enoic acid (106 mg, 0.64 mmol) and piperazin-1-yl(pyrrolidin-1-yl)methanone (125 mg, 0.68 mmol) were dissolved in DCM (5.0 mL), and DIPEA (111 mg, 0.85 mmol) was added. The mixture was stirred at rt for 2 h. Subsequently, the compound from Example 15A (150 mg, 0.43 mmol), DIPEA (55 mg, 0.43 mmol) and EDCI (82 mg, 0.43 mmol) were added. The reaction was stirred at 50° C. overnight. Then, water was added, and the mixture was extracted three times with DCM. The combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo, and the residue was purified by preparative HPLC to yield 25 mg (10%) of the title compound.

Aufarbeitung

  1. stirringThe reaction was stirred at 50° C. overnight
  2. extractionthe mixture was extracted three times with DCM
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-907f815ae1db4702b9a88f10da798df7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524722B2

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