Nitrogen → 1-[(3-Chloroquinoxalin-2-yl)amino]-4-methylpentan-2-one

HRID 389075Notes

Reaction equation

HRID 389075 reaction equation
[Cl:1][C:2]1[C:3]([NH:12][CH2:13][CH:14]([OH:19])[CH2:15][CH:16]([CH3:18])[CH3:17])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CCN(CC)CC.N#N>CS(C)=O>[Cl:1][C:2]1[C:3]([NH:12][CH2:13][C:14](=[O:19])[CH2:15][CH:16]([CH3:17])[CH3:18])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 947NitrogenHCID 8471TriethylamineHCID 859636751-[(3-Chloroquinoxalin-2-yl)amino]-4-methylpentan-2-ol

Product 1

HCID 859636811-[(3-Chloroquinoxalin-2-yl)amino]-4-methylpentan-2-oneYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2a (6.96 g, 24.8 mmol), 28.4 ml Et3N and sulphur trioxide trimethylamine complex (7.9 g, 56.8 mmol) in 28.4 ml DMSO, is stirred overnight (under N2) at room temperature, then ice water (50 ml) is added. The aqueous phase is extracted in CH2Cl2 (3×30 ml). The collected organic phases are dried (CaCl2) and then evaporated under reduced pressure. The residues are purified by chromatography on a silica column, eluent: C6H12/Et2O (85:15) to give a beige solid (4.18 g, 61%); 1H NMR (100 MHz, CDCl3) δ: 0.93 (s, 3H), 1.00 (s, 3H), 2.34 (m, 1H), 2.40 (s, 2H), 4.38 (d, 2H), 6.39 (t, 1H), 7.59 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.56, 25.01, 49.28, 51.55, 125.34, 125.87, 127.98, 130.14, 136.65, 137.92, 140.99, 147.30, 205.01. Analysis calculated for C14H16N3OCl: C, 60.54; H, 5.81; N, 15.13. Experimental: C, 60.32; H, 6.06; N, 14.95.

Workup

  1. extractionThe aqueous phase is extracted in CH2Cl2 (3×30 ml)
  2. dry with materialThe collected organic phases are dried (CaCl2)
  3. customevaporated under reduced pressure
  4. customThe residues are purified by chromatography on a silica column, eluent

Sources & evidence

ORD record
ord-3460dfac3dca4973a0a263db5cfa3326
Source dataset
uspto-grants-2013_02
Patent number
US08378098B2

Reaction notes

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