2-(((2S,3R)-1-(5-Chloro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione → ((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-chloro-2-(pyrimidin-2-yl)phenyl)methanone

HRID 61134Notes

Reaction equation

HRID 61134 reaction equation
NC[C@@H]1[C@H](C)CCCN1C(C1C=C(C)C=CC=1C1C=NN(C)C=1)=O.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:53]2[N:58]=[CH:57][CH:56]=[CH:55][N:54]=2)=[C:30]([CH:52]=1)[C:31]([N:33]1[CH2:38][CH2:37][CH2:36][C@@H:35]([CH3:39])[C@H:34]1[CH2:40][N:41]1C(=O)C2C(=CC=CC=2)C1=O)=[O:32]>>[NH2:41][CH2:40][C@@H:34]1[C@H:35]([CH3:39])[CH2:36][CH2:37][CH2:38][N:33]1[C:31]([C:30]1[CH:52]=[C:26]([Cl:25])[CH:27]=[CH:28][C:29]=1[C:53]1[N:54]=[CH:55][CH:56]=[CH:57][N:58]=1)=[O:32]

Participants

3

Reactant 2

HCID 1177276752-(((2S,3R)-1-(5-Chloro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dioneHCID 117728145((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone

Product 1

HCID 117728140((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-chloro-2-(pyrimidin-2-yl)phenyl)methanone

Procedure

The title compound was prepared following the same general protocol as described for ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(1-methyl-1H-pyrazol-4-yl)phenyl)methanone in Example A1 using 2-(((2S,3R)-1-(5-chloro-2-(pyrimidin-2-yl)benzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione. MS (ESI) 345 (M+H).

Sources & evidence

ORD record
ord-c52a022afda941638aac07ef1dc371d0
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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