2-Chloro-6-fluoro-1,3-benzoxazole → ((2S,3R)-2-(((6-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyridin-2-yl)phenyl)methanone

HRID 61066Notes

Reaction equation

HRID 61066 reaction equation
ClC1C=CC2OC(NC[C@@H]3[C@H](C)CCCN3C(OCC=C)=O)=NC=2C=1.[NH2:26][CH2:27][C@@H:28]1[C@H:33]([CH3:34])[CH2:32][CH2:31][CH2:30][N:29]1[C:35]([C:37]1[CH:42]=[C:41]([CH3:43])[CH:40]=[CH:39][C:38]=1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1)=[O:36].Cl[C:51]1[O:52][C:53]2[CH:59]=[C:58]([F:60])[CH:57]=[CH:56][C:54]=2[N:55]=1>>[F:60][C:58]1[CH:57]=[CH:56][C:54]2[N:55]=[C:51]([NH:26][CH2:27][C@@H:28]3[C@H:33]([CH3:34])[CH2:32][CH2:31][CH2:30][N:29]3[C:35]([C:37]3[CH:42]=[C:41]([CH3:43])[CH:40]=[CH:39][C:38]=3[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)=[O:36])[O:52][C:53]=2[CH:59]=1

Participants

4

Reactant 3

HCID 147488322-Chloro-6-fluoro-1,3-benzoxazoleHCID 117727920((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyridin-2-yl)phenyl)methanoneHCID 117732742(2S,3R)-Allyl 2-(((5-chlorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidine-1-carboxylate

Product 1

HCID 117728592((2S,3R)-2-(((6-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyridin-2-yl)phenyl)methanone

Procedure

The title compound was synthesized following the same general protocol as described for (2S,3R)-allyl 2-(((5-chlorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidine-1-carboxylate in Example A27, using ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyridin-2-yl)phenyl)methanone and 2-chloro-6-fluorobenzo[d]oxazole. ESI-MS (m/z): 459 [M+1]+.

Sources & evidence

ORD record
ord-17494a89a6594bc4a3f101aaa9fc715f
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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