Nitrogen → HCID 85963675, compound

HRID 389074Notes

Reaction equation

HRID 389074 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][CH2:14][CH:15]([OH:20])[CH2:16][CH:17]([CH3:19])[CH3:18].CCN(CC)CC.N#N>O1CCOCC1>[Cl:12][C:11]1[C:2]([NH:13][CH2:14][CH:15]([OH:20])[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 166592,3-DichloroquinoxalineHCID 183564841-Amino-4-methylpentan-2-ol

Product 1

HCID 85963675HCID 85963675, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,3-Dichloroquinoxaline (18.05 g, 90.7 mmol) is added to a solution of crude 1a (11.7 g, 99.8 mmol) and Et3N (19 ml, 13.8 g, 136 mmol) in dioxane (210 ml). The solution obtained is heated at reflux (under N2) for 6 h, it is then cooled to room temperature. Et3N, HCl is eliminated by filtration and the filtrate is concentrated under reduced pressure. The dark orange residue is purified by chromatography on a silica column, eluent: CH2Cl2/MeOH (100:0→99:1), to obtain a yellow solid (12.14 g, 48%); 1H NMR (100 MHz, CDCl3) δ: 0.72 (d, 3H), 0.78 (d, 3H), 1.60 (m, 3H), 3.68 (m, 4H), 5.82 (t, 1H), 7.58 (m, 4H); 13C NMR (25 MHz, CDCl3) δ: 22.17, 23.35, 24.60, 44.32, 48.62, 69.67, 125.30, 125.62, 127.91, 130.36, 136.52, 137.92, 140.59, 148.62. Analysis calculated for C14H18N3OCl: C, 60.10; H, 6.49; N, 15.02. Experimental: C, 59.87; H, 6.62; N, 15.25.

Workup

  1. customThe solution obtained
  2. temperatureis heated
  3. filtrationEt3N, HCl is eliminated by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe dark orange residue is purified by chromatography on a silica column, eluent

Sources & evidence

ORD record
ord-08f0a62759184ddda4128d791b845e7c
Source dataset
uspto-grants-2013_02
Patent number
US08378098B2

Reaction notes

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