6-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one → HCID 178518615, compound

HRID 1007540Notes

Reaction equation

HRID 1007540 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][NH2:12].[CH:13]1([C:20]2[CH:29]=[CH:28][C:23]3[NH:24][C:25](=[O:27])[O:26][C:22]=3[CH:21]=2)[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][NH:12][C@H:16]1[CH2:17][CH2:18][C@H:13]([C:20]2[CH:29]=[CH:28][C:23]3[NH:24][C:25](=[O:27])[O:26][C:22]=3[CH:21]=2)[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 226691222-Chloro-4-fluorobenzenepropanamine

Product 1

HCID 178518615HCID 178518615, compoundYield 21%

Procedure

Condensation of 3-(2-Chloro-4-fluorophenyl)-1-propylamine (1.5 g, 6.5 mmol) and ketone 5 (1.5 g, 6.5 mmol), following the procedure described in Example 1, gave 6-{trans-4-[3-(2-chloro-4-fluorophenyl)-propylamino]cyclohexyl}-3H-benzoxazol-2-one (535 mg, 21%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.41-7.35 (m, 2H), 7.17-7.13 (m, 2H), 6.99-6.94 (m, 2H), 3.60-2.90 (br s, 2H), 2.72 (t, J=8 Hz, 2H), 2.59 (t, J=8 Hz, 2H), 2.49-2.40 (m, 2H), 1.95 (br d, J=12 Hz, 2H), 1.77 (br d, J=12 Hz, 2H), 1.69-1.66 (m, 2H), 1.44 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.13 (dddd, J=13, 13, 13, 3 Hz, 2H).

Sources & evidence

ORD record
ord-27d0a3a47da7475f9f0c998164db1698
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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