2-Methoxyethylamine → 1-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid(2-methoxy-ethyl)-amide

HRID 523715

Reaction equation

HRID 523715 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[N:3]=1.F[P-](F)(F)(F)(F)F.N1([O+]=C(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:40][O:41][CH2:42][CH2:43][NH2:44].C(N(C(C)C)C(C)C)C>ClCCl>[CH3:40][O:41][CH2:42][CH2:43][NH:44][C:13]([C:4]1[N:3]=[C:2]([Cl:1])[C:11]2[C:6]([C:5]=1[OH:12])=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:15]

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 110205201-Chloro-4-hydroxyisoquinoline-3-carboxylic acidHCID 178484681HCID 178484681, compound

Product 1

HCID 114374721-Chloro-4-hydroxy-isoquinoline-3-carboxylic acid(2-methoxy-ethyl)-amideYield 15.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 45 mg (0.2 mmol) of 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid (from example A-1 d), 76 mg (0.2 mmol) of benzotriazol-1-yl-(bis-dimethylamino-methylene)-oxonium hexafluoro phosphate (HBTU), 18 μl 2-methoxy-ethylamine (0.2 mmol), and 1 ml of dichloromethane were added 96 μl (0.55 mmol) of ethyl-diisopropyl-amine with stirring. Stirring was continued at ambient temperature for 12 days. The product was isolated from the reaction mixture by flash column chromatography on silica gel using hexanes:ethyl acetate (9:1) as the eluent to give a white solid. 8.8 mg of the title compound were obtained; MS-(+)-ion: M+1=281.0.

Workup

  1. stirringStirring
  2. customThe product was isolated from the reaction mixture by flash column chromatography on silica gel
  3. customto give a white solid

Sources & evidence

ORD record
ord-878bd2518f7e4fe6ab95d7676ee89a21
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Linked notes

Loading…