Bromomethylcyclopropane → Ethyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 554903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 554903
Br[CH2:2][CH:3]1[CH2:5][C:4]1(F)F.C1(CBr)CC1.[CH3:13][C:14]1[N:15]=[C:16]([N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])[S:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH:5]1([CH2:4][N:26]2[CH2:27][CH2:28][N:24]([C:16]3[S:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]([CH3:13])[N:15]=3)[C:25]2=[O:29])[CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 81503BromomethylcyclopropaneHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Produkt 1

HCID 57919986Ethyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateAusbeute 96 %

Versuchsvorschrift

Following the procedure as described in Preparation 13, making variations as required to replace bromomethyl-2,2-difluorocyclopropane with cyclopropylmethyl bromide to react with ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained in 96% yield: 1H NMR (300 MHz, CDCl3) δ 4.23 (q, J=7.2 Hz, 2H), 4.07 (t, J=7.8 Hz, 2H), 3.67 (t, J=7.8 Hz, 2H), 3.16 (d, J=6.9 Hz, 2H), 2.58 (s, 3H), 1.28 (t, J=7.2 Hz, 3H), 0.97-0.88 (m, 1H), 0.59-0.42 (m, 2H), 0.25-0.12 (m, 2H); MS (ES+) m/z 310.3 (M+1).

Aufarbeitung

  1. customas described in Preparation 13

Quellen und Nachweise

ORD-Eintrag
ord-0565fad8572545c69626e2c852f89abd
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049016B2

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