Methyl Pyrrolidine-3-carboxylate → rac-1-{3-[(5-Methyl-pyridine-3-carbonyl)-amino]-benzyl}-pyrrolidine-3-carboxylic acid

HRID 1486723Notes

Reaction equation

HRID 1486723 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].ClC1C=CC(C(NC2C=CC=C(C3OCCO3)C=2)=O)=CC=1.N1CCC(C(OC)=O)C1.C([O:43][C:44]([CH:46]1[CH2:51][CH2:50][N:49]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([NH:59]C(=O)C3C=CC(Cl)=CC=3)[CH:54]=2)[CH2:48]C1)=[O:45])C>>[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([NH:59][C:55]2[CH:54]=[C:53]([CH:58]=[CH:57][CH:56]=2)[CH2:52][N:49]2[CH2:50][CH2:51][CH:46]([C:44]([OH:43])=[O:45])[CH2:48]2)=[O:8])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 4

HCID 4114360Methyl Pyrrolidine-3-carboxylateHCID 145380555-Methylnicotinoyl 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 131736810rac-1-{3-[(5-Methyl-pyridine-3-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 5-methylnicotinoyl 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. 45 min; [M+H]+=340.14.

Workup

  1. custom45 min

Sources & evidence

ORD record
ord-5ac2c87701e641e998a66a6acf8813af
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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