Hydrochloric Acid → 1-(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-1-methyl-ethylamine

HRID 1798506Notes

Reaction equation

HRID 1798506 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([NH:17]C(=O)C)([CH3:16])[CH3:15])[N:11]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:9]=2)[CH:5]=[N:6][CH:7]=1.Cl.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([NH2:17])([CH3:15])[CH3:16])[N:11]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68733910N-[1-(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-1-methyl-ethyl]-acetamide

Product 1

HCID 689465671-(5''-Bromo-[2,2';4',3'']terpyridin-6'-yl)-1-methyl-ethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[1-(5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-1-methyl-ethyl]-acetamide (Example 2.97; step1) (1 eq, 0.151 mmol, 62 mg) and SM HCl (20 eq, 3.01 mmol, 0.602 ml) are heated together at 100° C. overnight. The pH of the reaction mixture is adjusted to 8-9 by addition of sodium hydroxide (2M). The solution is dissolved in DCM and washed with water. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound; [M+H]+ 369/371

Workup

  1. washwashed with water
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e65024730c44558a22e70a7c88dfb31
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

Loading…