Triethylamine → tert-Butyl4-(2-{[4-(4-amino-3-chlorophenoxy)-2-pyridyl]amino}-2-oxoethyl)-1-piperidinecarboxylate

HRID 387814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387814
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[C:51]([O:55][C:56]([N:58]1[CH2:63][CH2:62][CH:61]([CH2:64][C:65](O)=[O:66])[CH2:60][CH2:59]1)=[O:57])([CH3:54])([CH3:53])[CH3:52]>C(OCC)(=O)C.O.CN(C)C=O>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:65](=[O:66])[CH2:64][CH:61]3[CH2:62][CH2:63][N:58]([C:56]([O:55][C:51]([CH3:53])([CH3:52])[CH3:54])=[O:57])[CH2:59][CH2:60]3)[CH:7]=2)=[CH:10][C:11]=1[Cl:16]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 229367984-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine

Produkt 1

HCID 22936879tert-Butyl4-(2-{[4-(4-amino-3-chlorophenoxy)-2-pyridyl]amino}-2-oxoethyl)-1-piperidinecarboxylateAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Amino-4-(4-amino-3-chlorophenoxy)pyridine (1.0 g), Bop reagent (1.9 g), triethylamine (1.2 ml), 2-[1-(tert-butoxycarbonyl)-4-piperidyl]acetic acid (1.0 g) and dimethylformamide (10 ml) were stirred at 60° C. for 2 hours and then at room temperature for 18 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (hexane:ethyl acetate=1:1) to obtain 570 mg of a light brown oil.

Aufarbeitung

  1. additionSilica gel was added to the extract solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with silica gel, and purification

Quellen und Nachweise

ORD-Eintrag
ord-500d486461444d61a5061c4393ad441a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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