Water → HCID 178453011, Verbindung

HRID 1171055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171055
[C:1]([C:3]1[C:4]([CH2:11][C:12]([NH:14][CH2:15][C:16]2[CH:32]=[CH:31][C:19]3[C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:21][O:22][C:18]=3[CH:17]=2)=[O:13])=[N+:5]([O-:10])[C:6](Cl)=[CH:7][CH:8]=1)#[N:2].[F:33][C:34]([F:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:35][NH2:36].C(Cl)Cl.O>CS(C)=O>[C:1]([C:3]1[C:4]([CH2:11][C:12]([NH:14][CH2:15][C:16]2[CH:32]=[CH:31][C:19]3[C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:21][O:22][C:18]=3[CH:17]=2)=[O:13])=[N+:5]([O-:10])[C:6]([NH:36][CH2:35][C:34]([F:43])([F:33])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 99641672,2-Difluoro-2-pyridin-2-ylethaneamineHCID 589729953-Cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-6-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide

Produkt 1

HCID 178453011HCID 178453011, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 3-cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-6-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide (29 mg) and 2,2-difluoro-2-pyridin-2-yl-ethylamine (20 mg) (Organic Process Research & Development 8:192-200, 2004), in DMSO (0.5 mL) was heated overnight at 80° C. LC/MS (ESI) indicated the mono-Boc product (M+H+ 580.1) as the major component. To the reaction vial was added DCM (10 mL) and water (3 mL). The mixture was vigorously stirred. After removing the aqueous layer, the organic layer was further washed with water (4×3 mL) to remove DMSO and water soluble components. Rotary evaporation of solvent afforded a syrupy residue that was used without purification. LCAMS (ESI) showed the mono-Boc product (M+H+ 580.1) as the major component and the di-Boc product (M+H+ 680.0) as a minor component.

Aufarbeitung

  1. customAfter removing the aqueous layer
  2. washthe organic layer was further washed with water (4×3 mL)
  3. customto remove DMSO and water soluble components
  4. customRotary evaporation of solvent
  5. customafforded a syrupy residue that
  6. customwas used without purification

Quellen und Nachweise

ORD-Eintrag
ord-89d5d2acffb040948bf6a42a327d8fa4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829584B2

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