1,2-Dichloroethane → HCID 178420050, compound

HRID 1678791Notes

Reaction equation

HRID 1678791 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[NH:28][NH2:29])[N:13]=2)=[CH:8][CH:7]=1.[NH:30]1[CH:34]=[C:33]([C:35](O)=O)[N:32]=[CH:31]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:35]([C:33]5[N:32]=[CH:31][NH:30][CH:34]=5)[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 594729242-[4-(1,3-dioxolan-2-yl)phenyl]-5-hydrazinyl-3-phenyl-1,6-NaphthyridineHCID 178524800HCID 178524800, compound

Product 1

HCID 178420050HCID 178420050, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-4 (0.2 g, 0.5 mmol), 1H-imidazole-4-carboxylic acid (0.06 g, 0.5 mmol), HOBT (0.06 g, 0.5 mmol), and DIEA (0.2 ml, 1.4 mmol) in DMF (2 ml) was added EDC (0.1 g, 0.6 mmol). The solution was stirred at room temperature for 45 min and was then heated at 80° C. in the microwave for 15 min. The solvent was removed in vacuo. The residue was taken up in DMF (0.5 ml) and was treated with glacial AcOH (2.0 ml). The reaction mixture was heated at 80° C. for 45 min. The reaction was then quenched with water (10 ml) and extracted into EtOAc (3×20 ml). The combined organic layers were concentrated in vacuo to give 22-1 as a brown residue.

Workup

  1. temperaturewas then heated at 80° C. in the microwave for 15 min
  2. customThe solvent was removed in vacuo
  3. additionwas treated with glacial AcOH (2.0 ml)
  4. temperatureThe reaction mixture was heated at 80° C. for 45 min
  5. customThe reaction was then quenched with water (10 ml)
  6. extractionextracted into EtOAc (3×20 ml)
  7. concentrationThe combined organic layers were concentrated in vacuo
  8. customto give 22-1 as a brown residue

Sources & evidence

ORD record
ord-74ae27bf952542258a3e650bf2b99a53
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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