6-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one → HCID 178518616, compound

HRID 1007524Notes

Reaction equation

HRID 1007524 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:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[CH2:26][CH2:27][CH2:28][NH2:29]>>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[CH2:26][CH2:27][CH2:28][NH:29][C@H:4]1[CH2:5][CH2:6][C@H: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)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 226691392,4-Difluoro-benzenepropanamine

Product 1

HCID 178518616HCID 178518616, compound

Procedure

Coupling of ketone 5 and 3-(2,4-difluorophenyl)-1-propylamine, using the method given in Example 1, gave (a) 6-{trans-4-[3-(2,4-difluorophenyl)-propylamino]-cyclohexyl}-3H-benzoxazol-2-one and (0.75 g, 37%), isolated as the HCl salt: 1H NMR (500 MHz, DMSO-d6): δ 11.49 (s, 1H), 8.84 (br s, 2H), 7.40 (ddd, J=9, 9, 7 Hz, 1H), 7.22-7.18 (m, 2H), 7.05 (ddd, J=8, 8, 2 Hz, 1H), 7.01 (dd, J=8, 1 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 3.11-3.02 (m, 1H), 2.98-2.92 (m, 2H), 2.70 (t, J=8 Hz, 2H), 2.56-2.49 (m, 1H), 2.18-2.11 (m, 2H), 1.96-1.86 (m, 4H), 1.51 (m, 4H), and

Sources & evidence

ORD record
ord-995a0a7e13564dd1b4cf5d15df04449d
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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