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

HRID 61053Notes

Reaction equation

HRID 61053 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[N:44]1[N:48]=[CH:47][CH:46]=[N:45]1)=[O:36].Cl[C:50]1[O:51][C:52]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][C:53]=2[N:54]=1>>[F:59][C:56]1[CH:57]=[CH:58][C:52]2[O:51][C:50]([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[N:44]3[N:48]=[CH:47][CH:46]=[N:45]3)=[O:36])=[N:54][C:53]=2[CH:55]=1

Participants

4

Reactant 3

HCID 141698172-Chloro-5-fluoro-1,3-benzoxazoleHCID 89740674((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanoneHCID 117732742(2S,3R)-Allyl 2-(((5-chlorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidine-1-carboxylate

Product 1

HCID 117728163((2S,3R)-2-(((5-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-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, ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone and 2-chloro-5-fluorobenzo[d]oxazole. ESI-MS (m/z): 449 [M+1]+.

Sources & evidence

ORD record
ord-f04076ebbb8f404faff8103b620317b1
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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