Water → HCID 10774329, compound

HRID 389079Notes

Reaction equation

HRID 389079 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:15][NH2:16].O.C(Cl)Cl.CO>CCO.ClCCl>[CH3:15][NH:16][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 962WaterHCID 6329Methylamine2×HCID 107745254-chloroimidazo[1,2-a]quinoxalineHCID 21226129Dichloromethane methanol

Product 1

HCID 10774329HCID 10774329, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 12 (0.110 g, 0.54 mmol) is solubilized in EtOH (10 ml), and then a solution of methylamine in water (40% by weight) (0.15 ml, 1.74 mmol) is introduced. The mixture is left under stirring in an autoclave, at room temperature, for at least 15 h. The product, initially insoluble, is solubilized shortly thereafter. The progression of the reaction is controlled by TLC, eluent: CH2Cl2/MeOH (95/5). At the end of 15 h, 1.5 eq (0.06 ml) of methylamine are added. After 5 h of stirring, the reaction progresses no further. The solvent is evaporated dry under vacuum. The yellowish residue obtained is solubilized in dichloromethane (10 ml). This organic phase is washed using a saturated sodium bicarbonate solution (10 ml) and then water (10 ml). It is then dried on Na2SO4 and then evaporated under vacuum. A white solid is recovered. The residue is purified on a silica gel column in order to eliminate traces of the starting product, eluent: CH2Cl2/AcEt (70/30). A white solid (0.99 g, 93%) is obtained; 1H NMR (300 MHz, DMSO-d6) δ: 7.92 (s, 1H, C—CH—N), 7.75 (dd, J1=1.22 Hz, J2=8.17 Hz, 1H, ArH), 7.65 (dd, J1=1.26 Hz, J2=8.06 Hz, 1H, ArH), 7.52 (s, 1H, N—CH—C), 7.4 (t, 1H, ArH), 7.25 (t, 1H, ArH), 6.15 (s, 1H, NH), 3.25 (d, 3H, —CH3); 13C NMR (200 MHz, DMSO-d6) δ: 142.25, 139.17, 131.99, 129.40, 128.17, 127.20, 125.14, 124.34, 114.14, 113.89, 29.20. Analysis calculated for C11H10N4: C, 66.65; H, 5.08; N, 28.26. Experimental: C, 66.26; H, 5.53; N, 28.23.

Workup

  1. waitThe mixture is left
  2. stirringAfter 5 h of stirring
  3. customThe solvent is evaporated
  4. customdry under vacuum
  5. customThe yellowish residue obtained
  6. washThis organic phase is washed
  7. customIt is then dried on Na2SO4
  8. customevaporated under vacuum
  9. customA white solid is recovered
  10. customThe residue is purified on a silica gel column in order

Sources & evidence

ORD record
ord-5ef19d6a98714b38891d1229685a333e
Source dataset
uspto-grants-2013_02
Patent number
US08378098B2

Reaction notes

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