6-(Aminomethyl)quinoline → Carbamic acid, N-[6-chloro-3-nitro-2-[(6-quinolinylmethyl)amino]-4-pyridinyl]-, 1,1-dimethylethyl ester

HRID 876856Notes

Reaction equation

HRID 876856 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[C:4]([Cl:19])[N:3]=1.[N:20]1[C:29]2[C:24](=[CH:25][C:26]([CH2:30][NH2:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>CC#N.CCN(CC)CC>[Cl:19][C:4]1[N:3]=[C:2]([NH:31][CH2:30][C:26]2[CH:25]=[C:24]3[C:29](=[CH:28][CH:27]=2)[N:20]=[CH:21][CH:22]=[CH:23]3)[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=1

Participants

5

Reactant 2

HCID 15143846-(Aminomethyl)quinolineHCID 86671448Tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate

Product 1

HCID 86672382Carbamic acid, N-[6-chloro-3-nitro-2-[(6-quinolinylmethyl)amino]-4-pyridinyl]-, 1,1-dimethylethyl esterYield 95.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A solution of tert-butyl 2,6-dichloro-3-nitropyridin-4-ylcarbamate (1.2 g, 3.9 mmol) and quinolin-6-ylmethanamine (616 mg, 3.9 mmol) in CH3CN (15 mL) and Et3N (1 mL) was stirred at 80° C. for 1 h. After cooled to room temperature, the mixture was concentrated. The residue was purified by chromatography to afford the title compound (1.60 g). MS (m/z): 430 (M+1)+.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-6756f73aad7841f18f9c75ef4472eb5c
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

Loading…