Methyl isothiocyanate → HCID 19785234, Verbindung

HRID 256674

Reaktionsgleichung

Reaktionsgleichung von HRID 256674
[N:1]([CH3:4])=[C:2]=[S:3].[NH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:17]3[C:22]([N:23]=2)=[CH:21][N:20]=[CH:19][N:18]=3)[CH2:10][CH2:9]1>O1CCCC1>[F:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:16]2[C:15]([NH:14][CH:11]3[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][NH:5][C:2]([NH:1][CH3:4])=[S:3])[CH2:13][CH2:12]3)=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][CH:21]=3)=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 11167Methyl isothiocyanateHCID 19785318N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine

Produkt 1

HCID 19785234HCID 19785234, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 0.7 parts of isothiocyanatomethane, 3.7 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine and 90 parts of tetrahydrofuran was stirred for 4 hours at room temperature. After evaporation, the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The first fraction was collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.3 parts (29%) of N-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]-N'-methylthiourea; mp. 205.5° C. (compound 179).

Aufarbeitung

  1. customAfter evaporation
  2. customthe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe first fraction was collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9295cb5107844e6fbcfdc0eb1c8f4178
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258380

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