5-Methylnicotinoyl chloride → rac-(2S*,4S*)-2-Methyl-1-{3-[(5-methyl-pyridine-3-carbonyl)-amino]-benzyl}-piperidine-4-carboxylic acid

HRID 1486727Notes

Reaction equation

HRID 1486727 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl[C:12]1[CH:31]=[CH:30][C:15]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[O:29]CC[O:26]3)[CH:20]=2)=O)=[CH:14][CH:13]=1.CC1CC(C(OC)=O)CC[NH:34]1.C(OC(C1CCN(CC2C=CC=C(NC(=O)C3C=CC(Cl)=CC=3)C=2)CC1)=O)C>>[CH3:24][CH:23]1[CH2:22][CH:21]([C:25]([OH:29])=[O:26])[CH2:20][CH2:19][N:18]1[CH2:16][C:15]1[CH:30]=[CH:31][CH:12]=[C:13]([NH:34][C:7]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)=[O:8])[CH:14]=1

Participants

5

Reactant 4

HCID 145380555-Methylnicotinoyl chlorideHCID 75300498Methyl 2-methylpiperidine-4-carboxylateHCID 867065474-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamideHCID 867065481-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 131736814rac-(2S*,4S*)-2-Methyl-1-{3-[(5-methyl-pyridine-3-carbonyl)-amino]-benzyl}-piperidine-4-carboxylic acid

Procedure

The title compound is prepared according to the reaction sequence 2.001a-2.001d described above using 5-methylnicotinoyl chloride instead of 4-chlorobenzoyl chloride as in 2.001a and rac-(2S*,4S*)-methyl 2-methylpiperidine-4-carboxylate instead of ethyl isonipecotate as in 2.001c: LC-MS A: tR=0.67 min; [M+H]+=422.08.

Sources & evidence

ORD record
ord-1919b8e8ada1444dba6c05728cf22760
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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