Dimethylformamide → 1-(5-(Benzyloxy)-7-cyanobenzo[d]thiazol-2-yl)-3-ethylurea

HRID 712268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712268
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Zn+2].C([O-])(=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:25]#[N:26])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 2

HCID 6228DimethylformamideHCID 578136291-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

Produkt 1

HCID 866639801-(5-(Benzyloxy)-7-cyanobenzo[d]thiazol-2-yl)-3-ethylureaAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 11192Zinc AcetateKatalysatorHCID 23994ZincKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-(5-(benzyloxy)-7-bromobenzo[d]thiazol-2-yl)-3-ethylurea (5.00 g, 12.29 mmol), zinc cyanide (1.58 g, 13.49 mmol), 1,1′-bis(diphenylphosphino)ferrocene (20 mg, 0.033 mmol), zinc acetate (90 mg, 0.50 mmol) and zinc dust (33.3 mg, 0.50 mmol) were stirred in a reaction tube in degassed DMF (60 ml) and water (600 ul). Tris(dibenzylideneacetone)dipalladium(0) (113.2 mg, 0.133 mmol) was added and the reaction purged with N2, sealed and heated to 100° C. for 18 h with stirring. LCMS indicated clean conversion to the desired material. The solvents were removed under reduced pressure, the resulting residue triturated with water, the solid collected by filtration and dried in a vacuum oven to afford the desired material as a pale white solid 4.4 g (100%). This material was used directly in the next step with no further purification.

Aufarbeitung

  1. customthe reaction purged with N2
  2. customsealed
  3. customThe solvents were removed under reduced pressure
  4. customthe resulting residue triturated with water
  5. filtrationthe solid collected by filtration
  6. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-c254583292a64119901cd80fe1599e1c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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