Hydrochloric Acid → HCID 178518608, compound

HRID 1007542Notes

Reaction equation

HRID 1007542 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]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][CH2:27][NH2:28].Cl>>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][CH2:27][NH:28][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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-oneHCID 226691352-Fluoro-benzenepropanaMine

Product 1

HCID 178518608HCID 178518608, compoundYield 45%

Procedure

Coupling of ketone 5 and 3-(2-fluorophenyl)-1-propylamine, using the method given in Example 1, gave 6-{trans-4-[3-(2-fluorophenyl)propylamino]-cyclohexyl}-3H-benzoxazol-2-one (1.7 g, 45%) as the HCl salt: 1H NMR (500 MHz, DMSO-d6): δ 11.50 (s, 1H), 8.86 (s, 2H), 7.34 (t, J=8 Hz, 1H), 7.35-7.26 (m, 1H), 7.19-7.15 (m, 3H), 7.02-6.97 (m, 2H), 3.10-3.03 (m, 1H), 2.98-2.92 (m, 2H), 2.72 (dd, J=8, 8 Hz, 2H), 2.57-2.50 (m, 1H), 2.18-2.13 (m, 2H), 1.98-1.92 (m, 2H), 1.89-1.85 (m, 2H), 1.57-1.46 (m, 4H).

Sources & evidence

ORD record
ord-66e40c92c29a4a9981107785c2c9bf25
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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