Carbamate → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(4-pyridylmethyl)-1H-imidazol-2-ylmethyl palmitoylcarbamate

HRID 1005556

Reaktionsgleichung

Reaktionsgleichung von HRID 1005556
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH2:22][OH:23])=[N:12][C:11]=2[CH:24]([CH3:26])[CH3:25])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])N.[C:31]([N:48]=[C:49]=[O:50])(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>>[C:31]([NH:48][C:49](=[O:50])[O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:24]([CH3:26])[CH3:25])[N:12]=1)(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Komponenten

4

Edukt 3

HCID 276CarbamateHCID 9844329{5-[(3,5-Dichlorophenyl)sulfanyl]-4-isopropyl-1-((pyridin-4-YL)methyl)imidazol-2-YL}methanolHCID 18792000Palmitoyl isocyanate

Produkt 1

HCID 696896135-(3,5-Dichlorophenylthio)-4-isopropyl-1-(4-pyridylmethyl)-1H-imidazol-2-ylmethyl palmitoylcarbamateAusbeute 50 %

Versuchsvorschrift

The compound 89 (245 mg, 0.6 mmol) was converted to the carbamate with palmitoyl isocyanate (5 eq.) in the same manner as the example 66 to give the compound 95 (207 mg, 50%) as oil. Rf 0.40 (EtOAc). PMR (CDCl3): δH0.88 (3 H, t like, CH3),1.25 (24 H, bs, --CH2 --), 1.31 (6 H, d, J 7.0 Hz, (CH3)2CH), 1.59 (2 H, m, --CH2 --), 2.59 (2 H, t, J 7.8 Hz, --CH2CO--, 3.19 (1 H, sep, J 7.0 Hz, (CH3)2CH), 5.22 (2 H, s, NCH2), 5.27 (2 H, s, OCH2), 6.70 (2 H, d, J 1.6 Hz, arom 2- and 6-H), 6.76 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.06 (1 H, t, J 1.6 Hz, arom 4-H), 7.35 (1 H, bs, NH), 8.46 (2 H, d-like, 4-pyridyl 3- and 5-H). IR (CHCl3)cm-1 3394 (NH), 1792 and 1764 (NCO), 1716 (NCOO). Elementary analysis (for C34H46N4O3SCl2) Calcd.: C, 62.69% H, 7.31% N, 8.12% S, 4.65% Cl, 10.28% Found: C, 61.89% H, 7.66% N, 8.41% S, 4.56% Cl, 9.65% hydrochloride of the compound 95 mp. 158-160° C. Elementary analysis (for C36H52N4O3SCl4) Calcd.: C, 56.69% H, 6.87% N, 7.35% S, 4.20% Cl, 18.59% Found: C, 55.85% H, 6.71% N, 7.64% S, 4.28% Cl, 18.66%

Quellen und Nachweise

ORD-Eintrag
ord-da94944aaee543b9ab3f8ffb4df6a2c6
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06054591

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