3-Cyclohexyl-L-alanine → (2S)-3-cyclohexyl-2-[(6-fluoro-1,3-benzoxazol-2-yl)amino]-N-{2-[(4-fluorophenyl)amino]ethyl}propanamide

HRID 347282Notes

Reaction equation

HRID 347282 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C@H:19]([NH2:23])[C:20]([OH:22])=O)[CH2:14][CH2:13]1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][CH2:32][CH2:33][NH2:34])=[CH:27][CH:26]=1>>[CH:15]1([CH2:18][C@H:19]([NH:23][C:2]2[O:3][C:4]3[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)[C:20]([NH:34][CH2:33][CH2:32][NH:31][C:28]2[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=2)=[O:22])[CH2:14][CH2:13][CH2:12][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 7124213-Cyclohexyl-L-alanineHCID 3016534N-(4-Fluorophenyl)ethylenediamineHCID 147488322-Chloro-6-fluoro-1,3-benzoxazole

Product 1

HCID 11247716(2S)-3-cyclohexyl-2-[(6-fluoro-1,3-benzoxazol-2-yl)amino]-N-{2-[(4-fluorophenyl)amino]ethyl}propanamide

Procedure

The title compound was prepared from 2-chloro-6-fluorobenzoxazole, L-cyclohexylalanine and N1-(4-fluoro-phenyl)-ethane-1,2-diamine.2HCl using the procedure analogous to that described in example 2. 1H NMR (DMSO-d6, 400 MHz) δ 8.18(m, 2H), 7.30(dd, 1H, J=2.4 Hz, J=8.6 Hz), 7.11(dd, 1H, J=4.8 Hz, J=8.4 Hz), 6.89(m, 1H), 6.84(m, 2H), 6.51(m, 2H), 4.28 (m, 1H), 3.15(m, 2H), 2.95(m, 2H), 1.55(m, 7H), 1.30(m, 1H), 1.05(m, 3H), 0.83(m, 2H). HPLC-MS calcd. for C24H28F2N4O2 (M+H+)443.22. found 443.4.

Sources & evidence

ORD record
ord-6feae01d97c445c195c729063bb614e5
Source dataset
uspto-grants-2007_02
Patent number
US07173051B2

Reaction notes

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