1,2-Dichloroethane → HCID 57805467, compound

HRID 2064432Notes

Reaction equation

HRID 2064432 reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([C:19]3([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:51][N:52]1[CH:56]=[C:55]([C:57](O)=[O:58])[N:54]=[CH:53]1>C(OCC)(=O)C.CN(C=O)C>[CH3:51][N:52]1[CH:56]=[C:55]([C:57]([NH:2][NH:1][C:3]2[N:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[C:6]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=2)=[N:8]3)=[O:58])[N:54]=[CH:53]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 57805468Tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 57805467HCID 57805467, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a round bottom flask was added tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-6) (3.94 g, 8.18 mmol), EDC (1.34 g, 10.6 mmol), HOBt (1.44 g, 10.6 mmol), 1-methyl-1H-imidazole-4-carboxylic acid (1.34 g, 10.6 mmol), and DMF (40 mL). The reaction mixture was heated to 60° C. while stirring under an atmosphere of nitrogen in a hot oil bath. After 45 minutes the reaction mixture was permitted to cool to room temperature, suspended in ethyl acetate, washed with a saturated solution of sodium bicarbonate, followed by water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give tert-butyl {1-[4-(5-{2-[(1-methyl-1H-imidazol-4-yl)carbonyl]hydrazino}-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-7) as red foam. MS (M+H)+: observed=590.3, calculated=590.69.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with a saturated solution of sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b5ee660103a4b1cad9dac688d71cf85
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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