Triethylamine → HCID 18449152, compound

HRID 1270150Notes

Reaction equation

HRID 1270150 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:13]([O:16]C)=[N:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=2.C(N(CC)CC)C.[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][CH2:35][CH2:36][NH2:37]>CN(C=O)C.CC(O)C.C(Cl)Cl.Br.CC(O)=O>[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][CH2:35][CH2:36][NH:37][C:2]1[C:3]2[N:4]([C:13](=[O:16])[NH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 14783666HCID 14783666, compoundHCID 15176215HCID 15176215, compound

Product 1

HCID 18449152HCID 18449152, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolventHCID 21966342Isopropanol methylene chlorideSolvent

Procedure

To a solution of 100 mg of 4,8-dichloro-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline and 109 mg of triethylamine in DMF (2.0 mL) was added 86 mg of N1-benzothiazol-2-yl-ethane-1,2-diamine. This solution was stirred at room temperature for 18 hrs. and then diluted with 10% IPA/methylene chloride, and washed with water and brine. The extracts were dried over sodium sulfate, filtered, and concentrated. The residue was separated by silica gel chromatography to provide a yellow solid. This solid was dissolved in a 1:1.5 mixture of 48% HBr/AcOH and refluxed for 2 hrs. The reaction mixture was concentrated and the residue was triturated with IPE to provide the hydrobromide salt of the title compound as a yellow solid. MS (M+H)+=412.2.

Workup

  1. washwashed with water and brine
  2. dry with materialThe extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was separated by silica gel chromatography
  6. customto provide a yellow solid
  7. temperaturerefluxed for 2 hrs
  8. concentrationThe reaction mixture was concentrated
  9. customthe residue was triturated with IPE

Sources & evidence

ORD record
ord-76a5a10943574ad09d8cb7b6725006ec
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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