5-Indanyl isocyanate → (S)-methyl 2-(5-(4-(3-(2,3-dihydro-1H-inden-5-yl)ureido)phenyl)oxazole-2-carboxamido)-3-methylbutanoate

HRID 1024462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024462
[N:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH2:8][CH2:7]2)=[C:2]=[O:3].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:24][C:23]([C:25]([NH:27][CH:28]([CH:33]([CH3:35])[CH3:34])[C:29]([O:31][CH3:32])=[O:30])=[O:26])=[N:22][CH:21]=2)=[CH:16][CH:15]=1>>[CH2:9]1[C:10]2[C:6](=[CH:5][C:4]([NH:1][C:2](=[O:3])[NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:24][C:23]([C:25]([NH:27][C@@H:28]([CH:33]([CH3:35])[CH3:34])[C:29]([O:31][CH3:32])=[O:30])=[O:26])=[N:22][CH:21]=4)=[CH:16][CH:15]=3)=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Komponenten

3

Edukt 2

HCID 50036815-Indanyl isocyanateHCID 67150345Methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate

Produkt 1

HCID 52936144(S)-methyl 2-(5-(4-(3-(2,3-dihydro-1H-inden-5-yl)ureido)phenyl)oxazole-2-carboxamido)-3-methylbutanoateAusbeute 92 %

Versuchsvorschrift

The title compound was synthesized analogous to Example 1, using 5-isocyanato-2,3-dihydro-1H-indene (84.87 mg, 0.533 mmol) and intermediate 1. Yield: 92%; 1H NMR (DMSO-d6, 300 MHz): δ 9.005-8.978 (d, 1H), 8.912 (s, 1H), 8.624 (s, 1H), 7.804 (s, 1H), 7.781-7.752 (d, J=8.7 Hz, 2H), 7.617-7.587 (d, J=9 Hz, 2H), 7.395 (s, 1H), 7.172-7.106 (m, 2H), 4.328-4.277 (m, 1H), 3.681 (s, 3H), 2.860-2.772 (m, 4H), 2.286-2.217 (m, 1H), 2.052-2.154 (m, 2H), 0.980-0.928 (d, J=6.9 Hz, 6H); MS (ESI) m/z 475 [M−H], 477 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-2d9cf289906543e6b86e0e2580876bcf
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

Notizen zur Reaktion

Wird geladen…