Methyl Pyrrolidine-3-carboxylate → rac-1-{3-[(6-Trifluoromethyl-pyridine-2-carbonyl)-amino]-benzyl}-pyrrolidine-3-carboxylic acid

HRID 1486725Notes

Reaction equation

HRID 1486725 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.ClC1C=CC(C(NC2C=CC=C(C3OCCO3)C=2)=O)=CC=1.N1CCC(C(OC)=O)C1.C([O:46][C:47]([CH:49]1[CH2:54][CH2:53][N:52]([CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([NH:62]C(=O)C3C=CC(Cl)=CC=3)[CH:57]=2)[CH2:51]C1)=[O:48])C>>[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[C:7]([C:9]([NH:62][C:58]2[CH:57]=[C:56]([CH:61]=[CH:60][CH:59]=2)[CH2:55][N:52]2[CH2:53][CH2:54][CH:49]([C:47]([OH:46])=[O:48])[CH2:51]2)=[O:10])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 4114360Methyl Pyrrolidine-3-carboxylateHCID 378634686-(Trifluoromethyl)pyridine-2-carbonyl chlorideHCID 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 131736812rac-1-{3-[(6-Trifluoromethyl-pyridine-2-carbonyl)-amino]-benzyl}-pyrrolidine-3-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 methyl pyrrolidine-3-carboxylate instead of ethyl isonipecotate as in 2.001c: LC-MS A: tR=0.64 min; [M+H]+=394.00.

Sources & evidence

ORD record
ord-2880dea902f74e90acb976c52bdcc3d1
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

Loading…