1,2-Dichloroethane → HCID 46916507, compound

HRID 2045942Notes

Reaction equation

HRID 2045942 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.[S:18]([CH2:22][CH2:23][C:24](O)=[O:25])(=[O:21])(=[O:20])[NH2:19].C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C>[NH2:19][S:18]([CH2:22][CH2:23][C:24]([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:25])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8072643-(2-quinoxalinyl)anilineHCID 27960291-Hydroxybenzotriazole hydrateHCID 217187673-Sulfamoylpropanoic acid

Product 1

HCID 46916507HCID 46916507, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (120 mg, 0.545 mol) and 3-sulfamoylpropanoic acid (100 mg, 0.654 mmol) in dry DMF (3 mL), EDC (115 mg, 0.6 mmol) and HOBt hydrate (92 mg, 0.6 mmol) were added and the reaction mixture stirred at room temperature for 24 hrs. The solvent was evaporated in vacuo (45° C., 0.1 mbar) and the residue was triturated with DCM (10 mL) and filtered. The solid was triturated with hot acetonitrile, filtered hot and dried to afford 3-(aminosulfonyl)-N-[3-(2-quinoxalinyl)phenyl]propanamide (78 mg, 40%). LCMS calculated for C17H16N4O3S (M+H): 357.41. found 357.24. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.41 (1H, br.), 9.50 (1H, s), 8.53 (1H, m), 8.15 (2H, m), 8.02 (1H, m), 7.94-7.80 (3H, m), 7.55 (1H, m), 6.88 (2H, br.), 3.35 (2H, t, J=7.2 Hz), 2.85 (2H, t, J=7.2 Hz).

Workup

  1. customThe solvent was evaporated in vacuo (45° C., 0.1 mbar)
  2. customthe residue was triturated with DCM (10 mL)
  3. filtrationfiltered
  4. customThe solid was triturated with hot acetonitrile
  5. filtrationfiltered hot
  6. customdried

Sources & evidence

ORD record
ord-75f1cf1e3555441a962ab91b71f5891c
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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