1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58116824, Verbindung

HRID 38600

Reaktionsgleichung

Reaktionsgleichung von HRID 38600
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[CH3:8][N:9]([CH3:18])[C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].CCN(C(C)C)C(C)C.[Cl:28][C:29]1[CH:30]=[C:31]([NH:36][C:37]2[C:38]3[C:45]4[CH2:46][CH2:47][NH:48][CH2:49][C:44]=4[S:43][C:39]=3[N:40]=[CH:41][N:42]=2)[CH:32]=[CH:33][C:34]=1[Cl:35].CCN=C=NCCCN(C)C>C(Cl)Cl.O>[Cl:28][C:29]1[CH:30]=[C:31]([NH:36][C:37]2[C:38]3[C:45]4[CH2:46][CH2:47][N:48]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:15]5[CH2:14][CH2:13][N:12]([C:10]([N:9]([CH3:18])[CH3:8])=[O:11])[CH2:17][CH2:16]5)[CH2:49][C:44]=4[S:43][C:39]=3[N:40]=[CH:41][N:42]=2)[CH:32]=[CH:33][C:34]=1[Cl:35]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531Diisopropylethylamine2×HCID 712909n,n-Dimethylpiperazine-1-carboxamideHCID 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 58116824HCID 58116824, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(2E)-4-Bromobut-2-enoic acid (106 mg, 0.64 mmol) and piperazine-1-carboxylic acid dimethylamide (107 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 mixture was stirred at rt 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 59 mg (24%) of the title compound.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt 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-3db0a56a8e02415888246276a89874c5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524722B2

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