Methanesulfonyl chloride → N-{2-[(6S)-2-Oxo-6-phenyl-3-{(1S)-1-[4-(pyridin-3-yl)phenyl]ethyl}-1,3-oxazinan-6-yl]ethyl}methanesulfonamide

HRID 1046122Notes

Reaction equation

HRID 1046122 reaction equation
[NH2:1][CH2:2][CH2:3][C@@:4]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>>[O:10]=[C:8]1[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5][C@:4]([CH2:3][CH2:2][NH:1][S:32]([CH3:31])(=[O:34])=[O:33])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:9]1

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58485301HCID 58485301, compound

Product 1

HCID 57346738N-{2-[(6S)-2-Oxo-6-phenyl-3-{(1S)-1-[4-(pyridin-3-yl)phenyl]ethyl}-1,3-oxazinan-6-yl]ethyl}methanesulfonamide

Procedure

The title compound was prepared from (R)-6-(2-aminoethyl)-6-phenyl-3-((S)-1-(4-(pyridin-3-yl)phenyl)ethyl)-1,3-oxazinan-2-one by treatment with MeSO2Cl. LC-MS Method 2 tR=1.525 min, m/z=480.2; 1H NMR (CDCl3) 1.52 (d, 3H), 2.05-2.32 (m, 6H), 2.81 (s, 3H), 2.86 (m, 1H), 2.93-3.04 (m, 1H), 3.06-3.20 (m, 1H), 4.73 (s, 1H), 5.63 (q, 1H), 6.95 (d, 2H), 7.05-7.22 (m, 2H), 7.23-7.40 (m, 6H), 7.71 (d, 1H), 8.50 (d, 1H), 8.66 (s, 1H).

Sources & evidence

ORD record
ord-50ddef010f1e4036b46515bbbcaeda78
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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