1,2-Dichloroethane → HCID 57805514, compound

HRID 2064444Notes

Reaction equation

HRID 2064444 reaction equation
[CH2:1](Cl)[CH2:2]Cl.C1C=CC2N(O)N=NC=2C=1.C(O)(=O)C.[NH:19]([C:21]1[N:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[C:24]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:25]([C:31]1[CH:36]=[CH:35][C:34]([C:37]3([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=1)=[N:26]2)[NH2:20].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O.O.C(Cl)Cl>[CH3:1][C:2]1[N:30]2[C:21]([C:22]3[CH:23]=[C:24]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:25]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:40][CH2:39][CH2:38]5)=[CH:33][CH:32]=4)=[N:26][C:27]=3[CH:28]=[CH:29]2)=[N:19][N:20]=1

Participants

10

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 57805468Tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 57805514HCID 57805514, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a round bottom flask was added EDC (4.63 g, 24.17 mmol), HOBt (3.27 g, 24.17 mmol), anhydrous DCM (50 mL) and acetic acid (13.2 mL, 13.86 mmol). The reaction mixture was then stirred at room temperature under an atmosphere of nitrogen for 30 minutes. Then added tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-6) (10.58 g, 21.97 mmol). The reaction mixture was then permitted to stir overnight (18 hours) at room temperature under an atmosphere of nitrogen, then heated to 80° C. for 2 hours. The reaction mixture was then suspended in ethyl acetate, slowly poured into a saturated solution of sodium bicarbonate, followed by water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography 1-20% IPA/DCM. The appropriate fractions were combined and the solvent was removed in vacuo to give tert-butyl {1-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-6f) as a tan solid. MS (M+H)+: observed=506.2, calculated=506.6.

Workup

  1. stirringto stir overnight (18 hours) at room temperature under an atmosphere of nitrogen
  2. temperatureheated to 80° C. for 2 hours
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography 1-20% IPA/DCM
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d03e7aca0d4e4ff584081652b9b4f2d1
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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