Potassium Carbonate → 4-(3-Benzyloxyphenyl)-N-(2,2,2-trifluoroethanesulfonyl)pyrid-3-ylmethylamine

HRID 392402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392402
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:21][NH2:22])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:31])([F:30])[CH2:25][S:26](Cl)(=[O:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:21][NH:22][S:26]([CH2:25][C:24]([F:31])([F:30])[F:23])(=[O:28])=[O:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 867595384-(3-Benzyloxyphenyl)pyridin-3-ylmethylamine

Produkt 1

HCID 867595374-(3-Benzyloxyphenyl)-N-(2,2,2-trifluoroethanesulfonyl)pyrid-3-ylmethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21470604DCE PyridineLösungsmittel

Versuchsvorschrift

A solution of N-(4-(3-benzyloxyphenyl)pyridin-3-ylmethylamine (1.0 equiv.) in 2:1 DCE/Pyridine (0.15 M) was cooled to 0° C. and treated with 2,2,2-trifluoroethanesulfonyl chloride (1.8 equiv.). The mixture was allowed to warm to ambient temperature and stir overnight. The reaction was treated with anhydrous potassium carbonate, stirred for 40 min, and filtered. The filtrate was purified via preparative HPLC eluting with 70:30 to 60:40 DCM/ethyl acetate, evaporated, and then triturated with diethyl ether to give the title compound. Anal Calcd for C21H19F3N2O3S: C, 57.79; H, 4.39; N, 6.42. Found: C, 57.60; H, 4.47; N, 6.41. 1H NMR (400 MHz) 3.77 (2H, q, J=9.0 Hz), 4.86 (2H, d), 4.99 (2H, d), 6.82 (2H, m), 6.95 (1H, m), 7.25 (2H, m), 7.34-7.40 (5H, m), 7.67 (1H, td, J=2.0, 8.0 Hz), 8.32 (1H, bs), 8.50 (1H, d, J=4.0 Hz). MS found 437.1 [M+H]+

Aufarbeitung

  1. stirringstirred for 40 min
  2. filtrationfiltered
  3. customThe filtrate was purified via preparative HPLC
  4. washeluting with 70:30 to 60:40 DCM/ethyl acetate
  5. customevaporated
  6. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2e5cda9fc058434c880e2d18915f871f
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800651B2

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