6-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one → HCID 178518617, compound

HRID 1007536Notes

Reaction equation

HRID 1007536 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.[F:18][C:19]1[CH:20]=[C:21]([CH2:26][CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[F:25]>>[F:18][C:19]1[CH:20]=[C:21]([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:22]=[CH:23][C:24]=1[F:25]

Participants

3

Reactant 2

HCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 226691243,4-Difluoro-benzenepropanamine

Product 1

HCID 178518617HCID 178518617, compoundYield 37%

Procedure

Coupling of ketone 5 and 3-(3,4-difluorophenyl)-1-propylamine, using the method given in Example 1, gave 6-(trans-4-[3-(3,4-difluorophenyl)-propylamino]cyclohexyl}-3H-benzoxazol-2-one (690 mg, 37%): 1H NMR (500 MHz, DMSO-d6): δ 7.33-7.24 (m, 2H), 7.12 (d, J=1 Hz, 1H), 7.06-7.02 (m, 1H), 6.98-6.93 (m, 2H), 3.51-3.10 (br s, 2H), 2.62 (dd, J=8, 8 Hz, 2H), 2.55 (dd, J=7, 7 Hz, 2H), 2.48-2.38 (m, 2H), 1.98-1.91 (m, 2H), 1.80-1.73 (m, 2H), 1.71-1.65 (m, 2H), 1.44 (dddd, J=10, 10, 10, 3 Hz, 2H), 1.13 (dddd, J=10, 10, 10, 3 Hz, 2H).

Sources & evidence

ORD record
ord-73e366dc8fc842f28ad3b61320e2426e
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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