2-Bromo-N-tert-butyl-1,3-thiazole-5-carboxamide → N-tert-butyl-2-((S)-3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidin-1-yl)thiazole-5-carboxamide

HRID 884370Notes

Reaction equation

HRID 884370 reaction equation
[OH:1][C:2]([CH3:24])([CH3:23])[CH2:3][C@@:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:6][CH2:5]1.Br[C:26]1[S:27][C:28]([C:31]([NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:29][N:30]=1>>[C:34]([NH:33][C:31]([C:28]1[S:27][C:26]([N:13]2[CH2:14][CH2:15][CH2:16][C@H:11]([N:7]3[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:24])[CH3:23])([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[O:9][C:8]3=[O:10])[CH2:12]2)=[N:30][CH:29]=1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

3

Reactant 2

HCID 203285472-Bromo-N-tert-butyl-1,3-thiazole-5-carboxamideHCID 58278645(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one

Product 1

HCID 58278666N-tert-butyl-2-((S)-3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidin-1-yl)thiazole-5-carboxamide

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one and 2-bromo-N-tert-butylthiazole-5-carboxamide following a procedure analogous to that described in Example 13. LC-MS Method 2 tR=1.23 min, m/z=515.

Sources & evidence

ORD record
ord-732bb75812624ef5b62364cbb81a5139
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

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