6-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one → HCID 178518618, compound

HRID 1007535Notes

Reaction equation

HRID 1007535 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH2:12])[CH:5]=[C:6]([F:8])[CH:7]=1.[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>>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C@H:16]2[CH2:17][CH2:18][C@H:13]([C:20]3[CH:29]=[CH:28][C:23]4[NH:24][C:25](=[O:27])[O:26][C:22]=4[CH:21]=3)[CH2:14][CH2:15]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 140499133-(3,5-Difluorophenyl)propan-1-amine

Product 1

HCID 178518618HCID 178518618, compoundYield 26%

Procedure

Condensation of 3-(3,5-difluorophenyl)-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-(3,5-difluorophenyl)propylamino]cyclohexyl}-3H-benzoxazol-2-one (640 mg, 26%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.13 (s, 1H), 7.01-6.92 (m, 5H), 2.66 (t, J=8 Hz, 2H), 2.57 (t, J=8 Hz, 2H), 2.49-2.40 (m, 2H), 1.95 (br d, J=10 Hz, 2H), 1.78 (br d, J=10 Hz, 2H), 1.74-1.68 (m, 2H), 1.45 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.14 (dddd, J=13, 13, 13, 3 Hz, 2H).

Sources & evidence

ORD record
ord-633a10f26ab44817895041914344123b
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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