1,2-Dichloroethane → HCID 68953028, compound

HRID 1453880Notes

Reaction equation

HRID 1453880 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:18]([OH:20])=O)=[N:5][N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH3:16])[C:8](=[O:17])[C:7]=12.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[F:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][NH2:50])=[CH:47][CH:46]=1>CN(C=O)C>[F:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][NH:50][C:18]([C:4]2[C:3]([O:2][CH3:1])=[C:7]3[C:8](=[O:17])[N:9]([CH3:16])[C:10]4[C:15]([N:6]3[N:5]=2)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:20])=[CH:47][CH:46]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 673264-FluorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68953295HCID 68953295, compound

Product 1

HCID 68953028HCID 68953028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxy-5-methyl-4-oxo-4,5-dihydropyrazolo[1,5-a]quinoxaline-2-carboxylic acid (75 mg, 0.27 mmol) in DMF were added HOBT (46 mg, 0.3 mmol), EDC (76 mg, 0.4 mmol), DIEA (0.05 mL, 0.29 mmol), and 4-fluorobenzylamine (50 mg, 0.4 mmol). The reaction mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and aqueous sodium bicarbonate. The EtOAc layer was dried (MgSO4), filtered and the solvent was removed under reduced pressure. The residue was triturated in MeOH to give the product as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 8.91 (t, J=5.9 Hz, 1H), 8.26 (d, J=8.0 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.39-7.44 (m, 3H), 7.17 (t, J=8.9 Hz, 2H), 4.49 (d, J=6.1 Hz, 2H), 4.02 (s, 3H), 3.61 (s, 3H); ES MS (M+1)=381.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and aqueous sodium bicarbonate
  3. dry with materialThe EtOAc layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was triturated in MeOH

Sources & evidence

ORD record
ord-14bd0b080d1e4997a14ea6f2b408afd9
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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