alpha-Methylhydrocinnamic acid → 2-methyl-3-phenyl-N-[2-(4-pyridyl)-1,3-benzoxazol-5-yl]propanamide

HRID 64237

Reaktionsgleichung

Reaktionsgleichung von HRID 64237
[CH3:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=O.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH:28]=1>>[CH3:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([NH:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)=[N:19][C:18]=2[CH:28]=1)=[O:5]

Komponenten

3

Edukt 2

HCID 99862alpha-Methylhydrocinnamic acidHCID 7360092-Pyridin-4-yl-benzooxazol-5-ylamine

Produkt 1

HCID 716625862-methyl-3-phenyl-N-[2-(4-pyridyl)-1,3-benzoxazol-5-yl]propanamideAusbeute 75 %

Versuchsvorschrift

Similarly prepared as per compound 8 procedure, using starting materials 2-methyl-3-phenylpropanoic acid and compound 4 to obtained title compound as white solid (75%). 1H NMR (CDCl3, 400 MHz) δ 1.29 (d, J=6 Hz, 3H), 2.63 (q, J=6.4 Hz, 1H), 2.77 (dd, J1=16 Hz, J2=5.6 Hz, 1H), 3.02 (dd, J1=16 Hz, J2=9.2 Hz, 1H), 7.17-7.25 (m, 5H), 7.34-7.44 (m, 3H), 7.75 (s, 1H), 7.99 (d, J=4 Hz, 2H), 8.75 (s, 2H); 13C NMR (CDCl3, 100 MHz) δ 18.0, 40.9, 44.9, 110.9, 112.5, 120.0, 121.2, 126.7, 128.8, 129.1, 134.4, 135.3, 139.8, 142.1, 147.8, 150.8, 174.3; ESI-HRMS for C22H20N3O2 (M+H)+ calcd. 358.1556 found 358.1556.

Quellen und Nachweise

ORD-Eintrag
ord-681ded67a57641febfcf30b3cd98633a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447134B2

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