Triethylamine → 4-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester

HRID 489187Notes

Reaction equation

HRID 489187 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18](Br)=[N:19][CH:20]=3)[C:15]2=[O:25])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:27]([N:30]1[CH:34]=[CH:33][N:32]=C1)[C:28]#[CH:29].C([N:37](CC)CC)C>CN(C)C=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([C:29]#[C:28][CH2:27][N:30]4[CH:34]=[CH:33][N:32]=[N:37]4)=[N:19][CH:20]=3)[C:15]2=[O:25])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 125919421-(prop-2-yn-1-yl)-1H-imidazoleHCID 865912014-(7-bromo-1-oxo-1H-6-azaisoquinolin-2-ylmethyl)benzoic acid tert-butyl ester

Product 1

HCID 102527494-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The coupling of 4-(7-bromo-1-oxo-1H-6-azaisoquinolin-2-ylmethyl)benzoic acid tert-butyl ester (0.70 g, 1.69 mmol) with 1-prop-2-ynyl-1H-imidazole (0.45 g, 4.22 mmol) using triethylamine (0.94 mL, 6.76 mmol), CuI (0.023 g, 0.12 mmol), and Pd(Ph3P)4 (0.08 g, 0.07 mmol) in dimethyl-formamide is carried out as described in Example 1, Step (2). The silica gel mesh is purified on a 3.5×18 cm silica gel column eluted with hexanes/ethyl acetate 1:1, methylene chloride/THF 7:1, then methylene chloride/THF 4:1. Evaporation and drying will afford the desired product.

Workup

  1. customThe silica gel mesh is purified on a 3.5×18 cm silica gel column
  2. washeluted with hexanes/ethyl acetate 1:1, methylene chloride/THF 7:1
  3. customEvaporation
  4. customdrying will

Sources & evidence

ORD record
ord-5ea1c9927b4b4bdc86b118a9f33ad96a
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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