Triethylamine → 2-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylthiazole-4-carboxamide

HRID 408851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408851
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[C:12]([NH:16][C:17]([C:19]1[N:20]=[C:21]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[S:22][CH:23]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][C:21]3[S:22][CH:23]=[C:19]([C:17]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[N:20]=3)[CH2:26][CH2:27]2)=[O:8])=[CH:4][C:3]=1[F:11]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 66661281N-tert-Butyl-2-(piperazin-1-ylmethyl)thiazole-4-carboxamide

Produkt 1

HCID 666616772-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylthiazole-4-carboxamideAusbeute 45,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-3-fluorobenzoic acid (0.703 g, 4.53 mmol), N-tert-butyl-2-(piperazin-1-ylmethyl)thiazole-4-carboxamide (1.28 g, 4.53 mmol) and triethylamine (0.459 g, 4.53 mmol, 0.630 mL) in dichloromethane was added 1-propanephosphonic acid cyclic anhydride (2.88 g, 4.53 mmol, 2.70 mL, 50% solution in ethyl acetate). The reaction was concentrated under reduced pressure and the residue was taken up in ethyl acetate, washed with sodium bicarbonate (×3) and brine. The organic phase was concentrated under reduced pressure to afford the title compound (0.87 g). MS (ESI) m/z 420.3 [M+H]+

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with sodium bicarbonate (×3) and brine
  3. concentrationThe organic phase was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-53b9735bee104731a6558542d51596c6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759352B2

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