6-(Trifluoromethyl)pyridine-2-carbonyl chloride → rac-(2S*,4S*)-2-Methyl-1-{3-[(6-trifluoromethyl-pyridine-2-carbonyl)-amino]-benzyl}-piperidine-4-carboxylic acid

HRID 1486726Notes

Reaction equation

HRID 1486726 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[C:7]([C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=1.Cl[C:15]1[CH:34]=[CH:33][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]3[O:32]CC[O:29]3)[CH:23]=2)=O)=[CH:17][CH:16]=1.CC1CC(C(OC)=O)CC[NH:37]1.C(OC(C1CCN(CC2C=CC=C(NC(=O)C3C=CC(Cl)=CC=3)C=2)CC1)=O)C>>[CH3:27][CH:26]1[CH2:25][CH:24]([C:28]([OH:32])=[O:29])[CH2:23][CH2:22][N:21]1[CH2:19][C:18]1[CH:33]=[CH:34][CH:15]=[C:16]([NH:37][C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:13])([F:12])[F:1])[N:8]=2)=[O:10])[CH:17]=1

Participants

5

Reactant 4

HCID 378634686-(Trifluoromethyl)pyridine-2-carbonyl 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 131736813rac-(2S*,4S*)-2-Methyl-1-{3-[(6-trifluoromethyl-pyridine-2-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 6-(trifluoromethyl)picolinoyl 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=0.49 min; [M+H]+=368.07.

Sources & evidence

ORD record
ord-0b553cb797d64df192d635900f23cb6a
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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