Methanol → HCID 69187894, Verbindung

HRID 1020274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020274
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:14][N:13]=[C:12]([CH2:15][NH:16][CH3:17])[N:11]=1)=[O:8].CO.[CH3:23][C:24]1[C:28]([CH:29]=O)=[C:27]([CH3:31])[O:26][N:25]=1.C([BH3-])#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:23][C:24]1[C:28]([CH2:29][N:16]([CH2:15][C:12]2[N:11]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=3)=[O:8])[S:14][N:13]=2)[CH3:17])=[C:27]([CH3:31])[O:26][N:25]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 2895763,5-Dimethyl-4-Isoxazolecarbaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 58055092HCID 58055092, Verbindung2×

Produkt 1

HCID 69187894HCID 69187894, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(3-Fluoro-benzyl)-3-(3-methylaminomethyl-[1,2,4]thiadiazol-5-yl)-urea (Intermediate XXVII) was taken up in DCM and methanol with 3,5-Dimethyl-isoxazole-4-carbaldehyde (2 eq.) and acetic acid (several drops). Reaction was stirred for several hours at ambient temperature. Sodium cyanoborohydride (2 eq.) was added at once and the reaction was stirred overnight at ambient temperature. An additional equivalent of 3,5-Dimethyl-isoxazole-4-carbaldehyde and sodium cyanoborohydride (2 eq.) was added and stirred 4 more hours. Crude r×n mixture was loaded directly onto a silica plug and eluted with 10% saturated NH3/MeOH in DCM. Purified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3) to give the title compound. 1H NMR (400 MHz, DMSO): 11.45 (br s, 1H), 7.43-7.35 (m, 2H), 7.17-7.05 (m, 3H), 4.38 (d, 2H), 3.58 (s, 2H), 3.33 (s, 2H), 2.31 (s, 3H), 2.16 (s, 3H), 2.15 (s, 3H).

Aufarbeitung

  1. customReaction
  2. stirringwas stirred overnight at ambient temperature
  3. stirringstirred 4 more hours
  4. washeluted with 10% saturated NH3/MeOH in DCM
  5. customPurified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3)

Quellen und Nachweise

ORD-Eintrag
ord-81710926290a45569c2e8327ca1ed29d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716320B2

Notizen zur Reaktion

Wird geladen…