Methyl isothiocyanate → 2-{6-[((3r)Oxolan-3-yl)amino]purin-9-yl}(4s,2r,3r,5r)-5-({[(cyclopentylamino)thioxomethyl]amino}methyl)oxolane-3,4-diol

HRID 1368857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1368857
[O:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@@H:16]2[O:20][C@H:19]([CH2:21][NH:22][C:23]([NH:25][CH3:26])=O)[C@@H:18]([OH:27])[C@H:17]2[OH:28])[CH2:2]1.CN=C=[S:32].CN=C=O.[CH:37]1([N:42]=[C:43]=[S:44])[CH2:41][CH2:40][CH2:39][CH2:38]1>>[O:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@H:17]([OH:28])[C@H:18]([OH:27])[C@@H:19]([CH2:21][NH:22][C:23]([NH:25][CH3:26])=[S:32])[O:20]2)[CH2:2]1.[O:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@H:17]([OH:28])[C@H:18]([OH:27])[C@@H:19]([CH2:21][NH:22][C:43]([NH:42][CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)=[S:44])[O:20]2)[CH2:2]1

Komponenten

6

Edukt 4

HCID 11167Methyl isothiocyanateHCID 12228Methyl Isocyanate2×HCID 141792Cyclopentyl isothiocyanateHCID 20592071n-[(5-{6-[((3r)Oxolan-3-yl)amino]purin-9-yl}(3s,2r,4r,5r)-3,4-dihydroxyoxolan-2-yl)methyl](methylamino)carboxamide2×

Produkt 2

HCID 205920232-{6-[((3r)Oxolan-3-yl)amino]purin-9-yl}(4s,2r,3r,5r)-5-({[(cyclopentylamino)thioxomethyl]amino}methyl)oxolane-3,4-diolHCID 205920272-{6[((3R)oxolan-3-yl)amino]purin-9-yl}(4S,2R,3R,5R)5-({[(methylamino)thioxomethyl]amino}methyl)oxolane-3,4diol

Versuchsvorschrift

Compound 77 was prepared in the manner of compound 24 substituting methyl isothiocyanate for methyl isocyanate and refluxing for 16 h [MS 410.3 (M+1)]. 2-{6-[((3R)oxolan-3-yl)amino]purin-9-yl}(4S,2R,3R,5R)-5-({[(cyclopentylamino)thioxomethyl]amino}methyl)oxolane-3,4-diol (78) Compound 78 was prepared in the manner of compound 24 substituting cyclopentyl isothiocyanate for methyl isocyanate and refluxing for 16 h [MS 464.3 (M+1)].

Aufarbeitung

  1. temperaturerefluxing for 16 h [MS 410.3 (M+1)]
  2. temperaturerefluxing for 16 h [MS 464.3 (M+1)]

Quellen und Nachweise

ORD-Eintrag
ord-6f80e9055d1142b2ad738acdb503f158
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06576620B2

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