1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178433764, Verbindung

HRID 2282226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2282226
Cl.Cl.[CH3:3][C:4]1[C:16]([C:17]2[S:18][C:19]([C:28]3[N:32]=[CH:31][NH:30][N:29]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:21]=2)=[C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH2:14][NH2:15])[CH:10]=[CH:11][N:6]2[N:5]=1.[CH3:33][N:34]1[CH:38]=[C:37]([C:39](O)=[O:40])[N:36]=[CH:35]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CCOC(C)=O.O.CN(C=O)C>[CH3:33][N:34]1[CH:38]=[C:37]([C:39]([NH:15][CH2:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][N:6]3[N:5]=[C:4]([CH3:3])[C:16]([C:17]4[S:18][C:19]([C:28]5[N:32]=[CH:31][NH:30][N:29]=5)=[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:21]=4)=[C:7]3[CH:8]=2)=[O:40])[N:36]=[CH:35]1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 178433763HCID 178433763, Verbindung

Produkt 1

HCID 178433764HCID 178433764, VerbindungAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-({2-methyl-3-[4-phenyl-5-(1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridin-5-yl}oxy)ethanamine di-hydrochloride (100 mg, 0.20 mmol) obtained in Example 73-B(i), TEA (1.5 mL), 1-methyl-1H-imidazole-4-carboxylic acid (120 mg, 0.95 mmol), HOBT (220 mg, 1.6 mmol), EDCI (350 mg, 1.8 mmol) and DMF (10 mL) was stirred at rt for 14 h. To the reaction mixture were added water (200 mL) and EtOAc (200 mL) and the mixture was stirred for 30 min. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was washed with EtOAc and diisopropyl ether, and dried to give the title compound (31 mg, 29%) as a yellow solid.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washThe residue was washed with EtOAc and diisopropyl ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b2f96d7d21c84672b8b91c3c550f1caf
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139589B2

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