Triethylamine → HCID 71466368, compound

HRID 1618933Notes

Reaction equation

HRID 1618933 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]#[CH:16].Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:13][CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]#[C:16][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8176303-Bromo-4-methylpyridineHCID 86713616HCID 86713616, compound

Product 1

HCID 71466368HCID 71466368, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

A solution of 4-chloro-1-(cyclopropylmethyl)-5-ethynyl-1H-benzotriazole (20 mg, 0.086 mmol), 3-bromo-4-methylpyridine (30 mg, 0.17 mmol), copper (I) iodide (5 mg, 0.026 mmol), and triethylamine (156 μL, 1.12 mmol) in DMF (0.54 mL) was sparged under nitrogen and heated at 90° C. for 18 hours. The mixture was treated with Quadrapure TU, stirred for 18 hours and filtered. The filtrated was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC, providing the titled compound: 1H-NMR (500 MHz, d6-DMSO) δ 8.78 (s, 1H), 8.53 (s, 1H), 8.05 (d, J=8.6 Hz, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.44 (s, 1H), 4.67 (d, J=7.3 Hz, 2H), 2.56 (s, 3H), 1.40 (m, 1H), 0.58 (d, J=7.7 Hz, 2H), 0.50 (d, J=5.0 Hz, 2H) ppm; high resolution mass spectrometry (ES+) m/z 323.1058 [(M+H)+; calculated for C18H16ClN4: 323.1058].

Workup

  1. additionThe mixture was treated with Quadrapure TU
  2. filtrationfiltered
  3. concentrationThe filtrated was concentrated in vacuo
  4. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-4a4eb702a6be4983956b1402bcba8e2d
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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