Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → tert-butyl-4-(N-{4-[4-(methylamino)-3-nitrophenoxy]-2-pyridyl}carbamoyl)piperidinecarboxylate

HRID 1963705

Reaktionsgleichung

Reaktionsgleichung von HRID 1963705
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:24]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:28]2C=CC=CC=2N=N1.[NH2:44][C:45]1[CH:50]=[C:49]([O:51][C:52]2[CH:57]=[CH:56][C:55](CN)=[C:54]([N+:60]([O-:62])=[O:61])[CH:53]=2)[CH:48]=[CH:47][N:46]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:44][C:45]2[CH:50]=[C:49]([O:51][C:52]3[CH:57]=[CH:56][C:55]([NH:24][CH3:28])=[C:54]([N+:60]([O-:62])=[O:61])[CH:53]=3)[CH:48]=[CH:47][N:46]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 69006232[4-(2-Amino(4-pyridyloxy))-2-nitrophenyl]methylamine

Produkt 1

HCID 69038249tert-butyl-4-(N-{4-[4-(methylamino)-3-nitrophenoxy]-2-pyridyl}carbamoyl)piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-(tert-butoxy)carbonylpiperidine-4-carboxylic acid (1 eq) in N,N-dimethyl formamide and N,N-disopropylethylamine (4 eq) was added BOP (2 eq) and the mixture was stirred at ambient temperature until homogeneous. To it was added [4-(2-amino(4-pyridyloxy))-2-nitrophenyl]methylamine (1 eq) and the resulting mixture was stirred at 60° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and the resulting tert-butyl-4-(N-{4-[4-(methylamino)-3-nitrophenoxy]-2-pyridyl}carbamoyl)piperidinecarboxylate was purified by silica gel chromatography. MS: MH+=472.2.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 60° C. for 16 h
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe resulting tert-butyl-4-(N-{4-[4-(methylamino)-3-nitrophenoxy]-2-pyridyl}carbamoyl)piperidinecarboxylate was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9d0fa942aa18481bb5415e11a6c1960f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415382B2

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