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Pyridine → HCID 178486235, Verbindung

HRID 1419237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1419237
N1C=CC=CC=1.[ClH:7].[CH3:8][NH:9][N:10]=[CH:11][NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.Cl.[C:23]([C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([CH2:36][C:37](=[O:39])[NH2:38])=[C:31](O)[CH:30]=[CH:29]2)(=[NH:25])[NH2:24].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(C(C)=O)C.O.C(O)(=O)C>[ClH:7].[ClH:7].[CH3:8][NH:9][N:10]=[CH:11][NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][C:31]2[CH:30]=[CH:29][C:28]3[C:33](=[CH:34][CH:35]=[C:26]([C:23](=[NH:24])[NH2:25])[CH:27]=3)[C:32]=2[CH2:36][C:37](=[O:39])[NH2:38])=[O:18])=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1364542706-Amidino-1-carbamoylmethyl-2-naphthol.hydrochlorideHCID 178486236HCID 178486236, Verbindung

Produkt 1

HCID 178486235HCID 178486235, VerbindungAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 131721204Methyl ethyl ketone acetic acid waterLösungsmittel

Versuchsvorschrift

20 Milliliters of 20% hydrous pyridine was added to 600 mg of 4-methylaminoiminomethylaminobenzoic acid.hydrochloride, 730 mg of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 646 mg of DCC and 32 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 48 hours at room temperature. The precipitate was filtered and the filtrate was concentrated under reduced pressure. To the residue was added 20 ml of DMF, and the solution was added dropwise to 300 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain a crude product. Then, the product was subjected to silica gel column chromatography using methyl ethyl ketone-water-acetic acid (80:15:5) as an eluent, and the desired fractions were collected and the solvent was distilled off under reduced pressure. To the residue were added 15 ml of methanol and 440 μl of concentrated hydrochloric acid, and the solution was added dropwise to a mixed liquid of 300 ml of acetone and 100 ml of ether, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 661.1 mg of the desired product.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. custom48 hours
  3. customat room temperature
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 20 ml of DMF
  7. additionthe solution was added dropwise to 300 ml of acetone
  8. stirringby stirring for 24 hours
  9. temperatureunder cooling with ice
  10. filtrationThen, the precipitate was collected by filtration
  11. customto obtain a crude product
  12. customthe desired fractions were collected
  13. distillationthe solvent was distilled off under reduced pressure
  14. additionTo the residue were added 15 ml of methanol and 440 μl of concentrated hydrochloric acid
  15. additionthe solution was added dropwise to a mixed liquid of 300 ml of acetone and 100 ml of ether
  16. stirringby stirring for 24 hours
  17. temperatureunder cooling with ice
  18. filtrationThen, the precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-df3f0fb29c0540689cd26b496fd583f6
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05885990

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