1,2-Dichloroethane → HCID 46916460, compound

HRID 2045936Notes

Reaction equation

HRID 2045936 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[C:18](O)(=[O:21])[CH2:19][OH:20].C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C>[OH:21][CH2:18][C:19]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757Glycolic AcidHCID 8072643-(2-quinoxalinyl)anilineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 46916460HCID 46916460, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (200 mg, 0.904 mol) and glycolic acid (83 mg, 1.085 mmol) in dry DMF (6 mL), EDC (191 mg, 1 mmol) and HOBt hydrate (154 mg, 1 mmol) were added and the reaction mixture was heated at 60° C. for 18 hrs. The solvent was evaporated in vacuo (45° C., 0.1 mbar) and the residue was dissolved in ethyl acetate (50 mL) and washed with water (2×25 mL). The organic phase was washed dried over sodium sulphate, filtered, the solvent evaporated in vacuo, the residue was triturated with DCM and further purified by preparative LCMS to afford 2-hydroxy-N-(3-(quinoxalin-2-yl)phenyl)acetamide (60 mg, 23% yield). LCMS calculated for C16H13N3O2 (M+H): 280.29. found 280. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.38 (1H, br.), 9.52 (1H, s), 8.62 (1H, m), 8.14-8.20 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 5.64 (1H, br), 4.08 (2H, s).

Workup

  1. customThe solvent was evaporated in vacuo (45° C., 0.1 mbar)
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with water (2×25 mL)
  4. washThe organic phase was washed
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customthe residue was triturated with DCM
  9. customfurther purified by preparative LCMS

Sources & evidence

ORD record
ord-c4a043a38051491ab465e9d0acf63194
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

Loading…