2,6-Dichlorobenzoxazole → (2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexyl-N-{2-[(4-fluorophenyl)amino]ethyl}propanamide

HRID 969790Notes

Reaction equation

HRID 969790 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[C:9]([Cl: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>>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:23][C@@H:19]([CH2:18][CH:15]3[CH2:14][CH2:13][CH2:12][CH2:17][CH2:16]3)[C:20]([NH:34][CH2:33][CH2:32][NH:31][C:28]3[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=3)=[O:22])[O:3][C:4]=2[CH:10]=1

Participants

4

Reactant 3

HCID 771752,6-DichlorobenzoxazoleHCID 7124213-Cyclohexyl-L-alanineHCID 3016534N-(4-Fluorophenyl)ethylenediamine

Product 1

HCID 11224927(2S)-2-[(6-chloro-1,3-benzoxazol-2-yl)amino]-3-cyclohexyl-N-{2-[(4-fluorophenyl)amino]ethyl}propanamide

Procedure

The title compound was prepared from 2,6-dichlorobenzooxazole, 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 8.30 (d, 1H, J=8.4 Hz), 8.17 (t, 1H, J=5.2 Hz), 7.46 (d, 1H, J=2.0 Hz), 7.13 (d, 1H, J=8.4 Hz), 7.08 (dd, 1H, J=8.4 Hz, J=2.0 Hz), 6.84(m, 2H), 6.51(m, 2H), 4.19(m, 1H), 3.15(m, 2H), 2.98(m, 2H), 1.55(m, 7H), 1.30(m, 1H), 1.05(m, 3H), 0.83(m, 2H). HPLC-MS calcd. for C24H28ClFN4O2(M+H+) 459.19, found 459.4.

Sources & evidence

ORD record
ord-bf289ba9704447afb09ec6225e5da381
Source dataset
uspto-grants-2007_12
Patent number
US07307095B2

Reaction notes

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