Propargylamine → HCID 22285037, compound

HRID 1061522Notes

Reaction equation

HRID 1061522 reaction equation
Cl[C:2]1[C:3]([Cl:16])=[N:4][C:5]2[CH:6]=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][C:10]=2[N:11]=1.[CH2:17]([NH2:20])[C:18]#[CH:19]>O1CCOCC1>[Cl:16][C:3]1[C:2]([NH:20][CH2:17][C:18]#[CH:19])=[N:11][C:10]2[CH:9]=[C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]3=[CH:6][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 9942937HCID 9942937, compound

Product 1

HCID 22285037HCID 22285037, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,3-dichlorobenzo[g]quinoxaline (0.634 g, 2.55 mmol), propargylamine (0.21 ml, 3.05 mmol) and TEA (0.53 mL, 3.83 mmol) in 15 mL of dioxane was heated to reflux for 4.5 hours. After evaporating the resulting mixture under vacuum, the crude product was chromatographed (CH2Cl2) to afford the title compound as a yellow solid (0.496 g, 73%); mp 169-172° C.; IR (KBr, cm−1) 3412, 3283, 3235, 1570, 1508, 1335; −1H NMR (DMSO) δ 8.44 (s, 1H), 8.26 (s,1H), 8.16-8.06 (m, 3H), 7.58-7.54 (m, 1H), 7.51-7.48 (m, 1H), 4.28 (dd, J=6.1, 2.5, 2H), 3.12 (t, J=2.5, 1H); LC/MS 97.8% (220 nm), m/z (M+H+) 268.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. customAfter evaporating the resulting mixture under vacuum
  4. customthe crude product was chromatographed (CH2Cl2)

Sources & evidence

ORD record
ord-5f618d96c68348d480ae4bd7bf643ec7
Source dataset
uspto-grants-2005_11
Patent number
US06960585B2

Reaction notes

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