4-Chloro-2-fluorophenyl isocyanate → (S)-methyl 2-(5-(4-(3-(4-chloro-2-fluorophenyl)ureido)phenyl)oxazole-2-carboxamido)-3-methylbutanoate

HRID 1024466

Reaktionsgleichung

Reaktionsgleichung von HRID 1024466
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])=[O:25])=[N:21][CH:20]=2)=[CH:15][CH:14]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][C:22]([C:24]([NH:26][C@@H:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])=[O:25])=[N:21][CH:20]=3)=[CH:15][CH:14]=2)=[C:4]([F:11])[CH:3]=1

Komponenten

3

Edukt 2

HCID 45582034-Chloro-2-fluorophenyl isocyanateHCID 67150345Methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate

Produkt 1

HCID 52932943(S)-methyl 2-(5-(4-(3-(4-chloro-2-fluorophenyl)ureido)phenyl)oxazole-2-carboxamido)-3-methylbutanoate

Versuchsvorschrift

The title compound was synthesized analogous to Example 1, using 4-chloro-2-fluoro-1-isocyanatobenzene (0.533 mmol) and intermediate 1. 1H-NMR (DMSO-d6, 300 MHz): δ 9.356 (s, 1H), 9.017-8.990 (d, 1H), 8.733 (s, 1H), 8.208-8.149 (m, 1H), 7.826 (s, 1H), 7.809-7.780 (d, J=8.7 Hz, 2H), 7.623-7.593 (d, J=9 Hz, 2H), 7.514-7.470 (d, J=2.1, 11.1 Hz, 1H), 7.270-7.241 (dd, J=0.6, 8.7 Hz, 1H), 4.328-4.277 (m, 1H), 3.680 (s, 3H), 2.286-2.217 (m, 1H), 0.979-0.957 (d, J=6.6 Hz, 6H); MS (ESI) m/z 487 (M−H), 489 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-33c9351b9654442ea0e6150c1762fb18
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722901B2

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