Diisopropylethylamine → 2-[(5-Cyano-pyridin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert butyl ester

HRID 2074397Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=1.C(N(C(C)C)CC)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 1502020tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate

HCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 865936772-[(5-Cyano-pyridin-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert butyl esterYield 52.3%

Procedure

The title compound (1.54 g) was prepared from (S)-2-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (2.0 g) and 2-chloro-5-cyanopyridine (1.29 g) in the presence of diisopropylethylamine (1.21 g) according to the method of D28.

Sources & evidence

ORD record: ord-b5ac4b19d1d6463696eca413b8bd59da
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919507B2

Reaction notes

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