1-Cyclobutylpropan-1-amine hydrochloride → [4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-propyl)-amine

HRID 1831522Notes

Reaction equation

HRID 1831522 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:11]=1[N+:24]([O-:26])=[O:25].Cl.[CH:28]1([CH:32]([NH2:35])[CH2:33][CH3:34])[CH2:31][CH2:30][CH2:29]1>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:35][CH:32]([CH:28]2[CH2:31][CH2:30][CH2:29]2)[CH2:33][CH3:34])[C:11]=1[N+:24]([O-:26])=[O:25]

Participants

3

Reactant 2

HCID 696580561-Cyclobutylpropan-1-amine hydrochlorideHCID 86591985Trifluoro-methanesulfonic acid 4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl ester

Product 1

HCID 22052220[4-(2-Chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-propyl)-amineYield 73%

Procedure

Trifluoro-methanesulfonic acid 4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl ester (0.50 g, 1.21 mmol), prepared substantially as described in Part C of Example 19a, and 1-cyclobutyl-propylamine HCl (0.36 g, 2.42 mmol) were treated substantially as described in Part C of Example 19a to produce 0.33 g (73%) of [4-(2-chloro-4-methoxy-phenyl)-3-nitro-pyridin-2-yl]-(1-cyclobutyl-propyl)-amine: MS (AP) m/z 375.9 [(M+H)+, 100].

Workup

  1. additionwere treated substantially

Sources & evidence

ORD record
ord-2a69b838f773459486b8598b12983b23
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

Loading…