6-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one → HCID 178429744, compound

HRID 1007544Notes

Reaction equation

HRID 1007544 reaction equation
[CH:1]1([C:8]2[CH:17]=[CH:16][C:11]3[NH:12][C:13](=[O:15])[O:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[CH3:18][C:19]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:26][CH2:27][CH2:28][NH2:29]>>[F:25][C:24]1[C:19]([CH3:18])=[C:20]([CH2:26][CH2:27][CH2:28][NH:29][C@H:4]2[CH2:5][CH2:6][C@H:1]([C:8]3[CH:17]=[CH:16][C:11]4[NH:12][C:13](=[O:15])[O:14][C:10]=4[CH:9]=3)[CH2:2][CH2:3]2)[CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 22669161HCID 22669161, compound

Product 1

HCID 178429744HCID 178429744, compoundYield 56%

Procedure

Coupling of ketone 5 and 3-(2-methyl-3-fluorophenyl)-1-propylamine, using the method given in Example 1, gave 6-{trans-4-[3-(3-fluoro-2-methylphenyl)propylamino]cyclohexyl}-3H-benzoxazol-2-one (1.4 g, 56%): 1H NMR (500 MHz, DMSO-d6): δ 7.16-7.10 (m, 2H), 7.01-6.93 (m, 4H), 2.65 (dd, J=8, 8 Hz, 2H), 2.60 (dd, J=7, 7 Hz, 2H), 2.49-2.39 (m, 2H), 2.18 (d, J=2 Hz, 3H), 1.98-1.93 (m, 2H), 1.81-1.75 (m, 2H), 1.68-1.61 (m, 2H), 1.45 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.13 (dddd, J=13, 13, 13, 3 Hz, 2H).

Sources & evidence

ORD record
ord-9fd0e9ce11ca46daafdc3315c59f7c54
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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