2-Chloropyridine → Tert-butyl 2-[methyl(pyridin-2-yl)amino]ethylcarbamate

HRID 607613Notes

Reaction equation

HRID 607613 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(CC)CC)C>C(#N)C.CO>[CH3:2][N:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 79772-ChloropyridineHCID 8471TriethylamineHCID 17750353Carbamic acid, N-[2-(methylamino)ethyl]-, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 59216311Tert-butyl 2-[methyl(pyridin-2-yl)amino]ethylcarbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl [2-(methylamino)ethyl]carbamate hydrochloride (0.30 g, 0.0014 mol), 2-chloropyridine (160 mg, 0.0014 mol), and triethylamine (300 μL, 0.0021 mol) in acetonitrile (5 mL) was heated at 90° C. overnight. The mixture was diluted with methanol, and purified by RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=252.1

Workup

  1. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-18386b0514f442d0b5bfc1b09ef3fa4f
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

Loading…