2-Fluorophenyl isocyanate → (R)-Methyl 1-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carbonyl)pyrrolidine-2-carboxylate

HRID 75828

Reaktionsgleichung

Reaktionsgleichung von HRID 75828
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([N:25]3[CH2:29][CH2:28][CH2:27][C@@H:26]3[C:30]([O:32][CH3:33])=[O:31])=[O:24])[O:20][N:19]=2)=[CH:14][CH:13]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:10])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([N:25]3[CH2:29][CH2:28][CH2:27][C@@H:26]3[C:30]([O:32][CH3:33])=[O:31])=[O:24])[O:20][N:19]=2)=[CH:14][CH:13]=1

Komponenten

3

Edukt 2

HCID 855882-Fluorophenyl isocyanateHCID 67353968(R)-methyl 1-(3-(4-aminophenyl)isoxazole-5-carbonyl)pyrrolidine-2-carboxylate

Produkt 1

HCID 67353309(R)-Methyl 1-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carbonyl)pyrrolidine-2-carboxylateAusbeute 58 %

Versuchsvorschrift

The title compound was prepared according to the procedure as set forth in example 151, except that 1-fluoro-2-isocyanatobenzene was used in place of 1-fluoro-3-isocyanatobenzene and (R)-methyl 1-(3-(4-aminophenyl)isoxazole-5-carbonyl)pyrrolidine-2-carboxylate was used in place of methyl 2-(3-(4-aminophenyl) isoxazole-5-carboxamido)-3-methylbutanoate to yield 58% of the title compound. MS (ES+): m/z 453 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 9.35 (s, 1H), 8.64 (s, 1H), 8.15 (m, 1H), 7.89 (d, 2H), 7.66 (s, 1H), 7.6 (d, 2H), 7.26 (m, 1H), 7.16 (m, 1H), 7.06 (m, 1H), 3.92 (t, 1H), 3.67 (s, 3H), 3.65 (m, 1H), 2.29 (m, 1H), 1.97 (m, 2H), 1.24 (m, 2H).

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-0a6a2f619de04136aaf7a6048980df6b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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