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Pyridine → 3-[6-(Azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-pyridin-2-yl-benzamide

HRID 600518
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600518
ClC(N(C)C)=C(C)C.[N:9]1([C:13]([C:15]2[N:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][C@H:32]4[CH2:36][CH2:35][N:34]([CH3:37])[C:33]4=[O:38])[CH:30]=3)[C:25](O)=[O:26])=[CH:17][CH:16]=2)=[O:14])[CH2:12][CH2:11][CH2:10]1.[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1.N1C=CC=CC=1>C(Cl)Cl>[N:9]1([C:13]([C:15]2[N:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][C@H:32]4[CH2:36][CH2:35][N:34]([CH3:37])[C:33]4=[O:38])[CH:30]=3)[C:25]([NH:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)=[O:26])=[CH:17][CH:16]=2)=[O:14])[CH2:12][CH2:11][CH2:10]1
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 104392-AminopyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 597611453-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid2×

Produkt 1

HCID 249526653-[6-(Azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-pyridin-2-yl-benzamide
Ausbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Chloro-N,N,2-trimethyl-prop-1-en-1-amine (0.077 mL, 0.58 mmol) was added to a solution of 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid (Intermediate 30) (200 mg, 0.49 mmol) in DCM (5 mL) and stirred at ambient temperature for 50 minutes. 2-Amino-pyridine (93 mg, 0.98 mmol) and pyridine (0.080 mL, 0.98 mmol) were added and the reaction stirred for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (40 mL), washed with water (10 mL), and brine (10 mL), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with a gradient of 0-100% methanol in DCM to afford the product (112 mg, 47%). 1H NMR δ (300 MHz, CDCl3) 2.12-2.26 (m, 1H), 2.35 (quintet, 2H), 2.53-2.66 (m, 1H), 2.93 (s, 3H), 3.34-3.57 (m, 2H), 4.25 (t, 2H), 4.70 (t, 2H), 4.93 (t, 1H), 6.97 (s, 1H), 7.08 (t, 1H), 7.22 (s, 1H), 7.38 (d, 1H), 7.45 (s, 1H), 7.75 (t, 1H), 8.11 (d, 1H), 8.29 (d, 1H), 8.33 (q, 2H), 8.68 (s, 1H); m/z 488 (M+H)+.

Aufarbeitung

  1. stirringthe reaction stirred for 16 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (40 mL)
  4. washwashed with water (10 mL), and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with a gradient of 0-100% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-22f90b432ce94e0c8ddf5658d11c2146
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902200B2

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