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2-amino-4-chloro-N-(5-chloropyridin-2-yl)benzamide → 2-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide

HRID 644183
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 644183
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[NH2:17])=[N:6][CH:7]=1.[C:19]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[C:25]([O:32][CH:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)[CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>N1C=CC=CC=1.ClCCl>[C:19]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:17][C:11]2[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=2[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:18])=[O:28])=[C:25]([O:32][CH:33]2[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]2)[CH:24]=1)([CH3:22])([CH3:20])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 219061992-amino-4-chloro-N-(5-chloropyridin-2-yl)benzamideHCID 866102604-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride

Produkt 1

HCID 685368592-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a stirring solution of N-(5-chloropyridin-2-yl)-2-amino-4-chlorobenzamide (0.74 g, 26.5 mmol) in pyridine (1 mL) and dichloromethane (20 mL) at 0° C. was added a solution of 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride (1.05 g, 26.5 mmol) in dichloromethane (10.5 mL). The cold bath was then removed and after 72 h, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed with water, followed by satd aq NaHCO3 and then brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel, eluting with a solution of 20% ethyl acetate in hexanes.

Aufarbeitung

  1. customThe cold bath was then removed and after 72 h
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was then dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed over silica gel
  9. washeluting with a solution of 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-90f705cff8e747bb95815b19c7abeb71
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07700628B2

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