7-bromo-3,3-dimethyl-1-piperidin-4-yl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one trifluoroacetate → 7-bromo-1-{1-[(3-fluoro-2'-{[(1R)-3-hydroxy-1-methylpropyl]oxy}biphenyl-4-yl)carbonyl]piperidin-4-yl}-3,3-dimethyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1026591Notes

Reaction equation

HRID 1026591 reaction equation
[Si]([O:18][CH2:19][CH2:20][C@H:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:35]=[CH:34][C:33]([C:36]([OH:38])=O)=[C:32]([F:39])[CH:31]=1)[CH3:22])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.[Br:47][C:48]1[CH:66]=[N:65][C:51]2[O:52][C:53]([CH3:64])([CH3:63])[C:54](=[O:62])[N:55]([CH:56]3[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]3)[C:50]=2[CH:49]=1>>[Br:47][C:48]1[CH:66]=[N:65][C:51]2[O:52][C:53]([CH3:63])([CH3:64])[C:54](=[O:62])[N:55]([CH:56]3[CH2:57][CH2:58][N:59]([C:36]([C:33]4[CH:34]=[CH:35][C:30]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[O:23][C@H:21]([CH3:22])[CH2:20][CH2:19][OH:18])=[CH:31][C:32]=4[F:39])=[O:38])[CH2:60][CH2:61]3)[C:50]=2[CH:49]=1

Participants

3

Reactant 2

HCID 680060047-bromo-3,3-dimethyl-1-piperidin-4-yl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one trifluoroacetateHCID 680062692'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylic acid

Product 1

HCID 680059947-bromo-1-{1-[(3-fluoro-2'-{[(1R)-3-hydroxy-1-methylpropyl]oxy}biphenyl-4-yl)carbonyl]piperidin-4-yl}-3,3-dimethyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Procedure

In accordance with the methods of Examples 13-4 and 5-5, the compound of Example 5-3 was used instead of the compound of Example 13-3, and the compound of Example 52-2 was used instead of the compound of Reference Example 3 to afford 7-bromo-1-{1-[(3-fluoro-2′-{[(1R)-3-hydroxy-1-methylpropyl]oxy}biphenyl-4-yl)carbonyl]piperidin-4-yl}-3,3-dimethyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one.

Sources & evidence

ORD record
ord-db96c64d58284384b6011e841d21c81a
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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