Cyanamide → 3-[cyano(methyl)sulfonimidoyl]-N-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-2-methylpropanamide

HRID 1803442

Reaktionsgleichung

Reaktionsgleichung von HRID 1803442
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([NH:14][C:15](=[O:21])[CH:16]([CH3:20])[CH2:17][S:18][CH3:19])=[C:11]([CH3:13])[N:12]=2)[CH:5]=[N:6][CH:7]=1.[N:22]#[C:23][NH2:24].IC1C=CC=C(CC([O-])=[O:34])C=1CC([O-])=O>ClCCl>[C:23]([N:24]=[S:18]([CH2:17][CH:16]([CH3:20])[C:15]([NH:14][C:10]1[S:9][C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:12][C:11]=1[CH3:13])=[O:21])([CH3:19])=[O:34])#[N:22]

Komponenten

5

Edukt 3

HCID 9864CyanamideHCID 219456882-[2-(Carboxylatomethyl)-3-iodophenyl]acetateHCID 59580474N-[2-(5-fluoro-pyridin-3-yl)-4-methyl-thiazol-5-yl]-2-methyl-3-methylsulfanyl-propionamide

Produkt 1

HCID 595805863-[cyano(methyl)sulfonimidoyl]-N-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-2-methylpropanamideAusbeute 75,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-[2-(5-fluoro-pyridin-3-yl)-4-methyl-thiazol-5-yl]-2-methyl-3-methylsulfanyl-propionamide (0.250 g, 0.76 mmol) in dichloromethane (3.07 ml) at 0° C. was added cyanamide (0.064 g, 1.53 mmol) and iodobenzenediacetate (0.272 g, 0.84 mmol) and subsequently stirred at room temperature for 1 hour. The reaction was concentrated to dryness. The crude material was purified by silica gel column chromatography (10% methanol/ethyl acetate) to give the desired product as a light yellow solid (0.220 g, 60%): mp 75-81° C.; 1H NMR (400 MHz, CDCl3) δ 9.85 (s, 1H), 8.94-8.70 (m, 1H), 8.57-8.34 (m, 1H), 8.07-7.77 (m, 1H), 3.69-3.40 (m, 2H), 3.22-3.00 (m, 1H), 2.92-2.77 (m, 3H), 2.50 (m, 3H), 1.49 (m, 3H); ESIMS m/z 363.9 (M-2).

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness
  2. customThe crude material was purified by silica gel column chromatography (10% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c822734113d44064b820de3c3a179629
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350044B2

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