[4-Carbamoyl-3-(2,5-difluoro-4-methyl-benzyloxy)-isothiazol-5-yl]carbamic acid phenyl ester → (R)-3-(2,5-Difluoro-4-methyl-benzyloxy)-5-(3-[4-(3-hydroxy-pyrrolidin-1-yl)-butyl]-ureido)-isothiazole-4-carboxylic acid amide

HRID 750581

Reaktionsgleichung

Reaktionsgleichung von HRID 750581
C1(O[C:8](=[O:29])[NH:9][C:10]2[S:14][N:13]=[C:12]([O:15][CH2:16][C:17]3[CH:22]=[C:21]([F:23])[C:20]([CH3:24])=[CH:19][C:18]=3[F:25])[C:11]=2[C:26](=[O:28])[NH2:27])C=CC=CC=1.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][C@@H:37]([OH:40])[CH2:36]1>>[F:25][C:18]1[CH:19]=[C:20]([CH3:24])[C:21]([F:23])=[CH:22][C:17]=1[CH2:16][O:15][C:12]1[C:11]([C:26]([NH2:27])=[O:28])=[C:10]([NH:9][C:8]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]2[CH2:39][CH2:38][C@@H:37]([OH:40])[CH2:36]2)=[O:29])[S:14][N:13]=1

Komponenten

3

Edukt 2

HCID 54330906[4-Carbamoyl-3-(2,5-difluoro-4-methyl-benzyloxy)-isothiazol-5-yl]carbamic acid phenyl esterHCID 57197635(R)-1-(4-amino-butyl)-pyrrolidin-3-ol

Produkt 1

HCID 68504906(R)-3-(2,5-Difluoro-4-methyl-benzyloxy)-5-(3-[4-(3-hydroxy-pyrrolidin-1-yl)-butyl]-ureido)-isothiazole-4-carboxylic acid amide

Versuchsvorschrift

The title compound was prepared from [4-carbamoyl-3-(2,5-difluoro-4-methyl-benzyloxy)-isothiazol-5-yl]-carbamic acid phenyl ester and (R)-1-(4-amino-butyl)-pyrrolidin-3-ol by the procedure analogous to Example 6. HPLC ret. time: 3.2 minutes. 1H NMR (400 MHz, CD3OD) δ 7.19 (dd, 1H, J=6.0, 9.2 Hz), 7.04 (dd, 1H, J=6.0, 10 Hz), 5.45 (s, 2H), 4.34 (m, 1H), 3.23 (m, 2H), 2.86 (dd, 1H, J=6.0, 10.4 Hz), 2.78 (m, 1H), 2.65-2.54 (m, 4H), 2.25 (s, 3H), 2.14 (m, 1H), 1.73 (m, 1H), 1.56 (m, 4H) ppm; MS (APCl, m/z): 484 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-18f90e010bfd42a0a21aa5ff64605a97
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405218B2

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