1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86281292, Verbindung

HRID 510222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510222
[C:1]1([C:7]2[C:8]3[CH2:16][CH2:15][NH:14][CH2:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCOC(C)=O>[Cl:17][C:18]1[C:26]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:14]1[CH2:15][CH2:16][C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12][CH:11]=[N:10][C:9]=2[CH2:13]1)=[O:21]

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 583781534-Phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Produkt 1

HCID 86281292HCID 86281292, VerbindungAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 1 (55 mg, 0.26 mmol) in DCM (3 mL) was added 2-chloro-3-(trifluoromethyl)benzoic acid (60 mg, 0.26 mmol) followed by EDCI (75 mg, 0.39 mmol), HOBt (28 mg, 0.21 mmol) and TEA (0.72 mL, 0.52 mmol). The mixture was stirred overnight and then loaded directly on a column. Chromatography on SiO2 eluting with EtOAc/Hex afforded the desired product as a colorless foam (80 mg, 73%). MS (ESI) mass calcd. C21H15ClF3N3O, 417.09. m/z found 418.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.16-9.03 (m, 1H), 7.82-7.77 (m, 1H), 7.65-7.46 (m, 7H), 5.16-5.02 (m, 1H), 4.61-4.42 (m, 1H), 4.09-3.97 (m, 1H), 3.52-3.38 (m, 1H), 3.11-2.83 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-8ac4a731e83745c8983bfd1830405ca4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096596B2

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