3-(2-Chloro-pyrimidin-4-yl)-benzaldehyde → 4(R)-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester

HRID 14937Notes

Reaction equation

HRID 14937 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[CH:5]=[CH:4][N:3]=1.[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][C@@H:29]([NH2:32])[C@@H:28]([CH3:33])[CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][C@@H:29]([NH:32][CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:9]=2)[C@@H:28]([CH3:33])[CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehydeHCID 67045008benzyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate

Product 1

HCID 866033194(R)-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester

Procedure

Intermediate 1 was coupled with 4(R)-amino-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester (prepared according to literature procedure (ref 1)) following procedure B. LC-MS showed the product had the expected M+H+ of 451.

Sources & evidence

ORD record
ord-57c8d44e4c6c472f8c6791b40d6d195e
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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