1,2-Dichloroethane → HCID 57805513, compound

HRID 2104118Notes

Reaction equation

HRID 2104118 reaction equation
[CH2:1](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(O)=O.[C:18]([O:22][C:23](=[O:53])[NH:24][C:25]1([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[C:44]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:43][C:42]4[C:37](=[CH:38][CH:39]=[N:40][C:41]=4[NH:51][NH2:52])[N:36]=3)=[CH:31][CH:30]=2)[CH2:28][CH2:27][CH2:26]1)([CH3:21])([CH3:20])[CH3:19]>C(OCC)(=O)C.CN1C(=O)CCC1.C(Cl)Cl>[C:18]([O:22][C:23](=[O:53])[NH:24][C:25]1([C:29]2[CH:30]=[CH:31][C:32]([C:35]3[C:44]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[CH:43][C:42]4[C:41]5=[N:51][N:52]=[CH:1][N:40]5[CH:39]=[CH:38][C:37]=4[N:36]=3)=[CH:33][CH:34]=2)[CH2:28][CH2:27][CH2:26]1)([CH3:21])([CH3:19])[CH3:20]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 284Formic AcidHCID 757711-HydroxybenzotriazoleHCID 57805468Tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 57805513HCID 57805513, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a round bottom flask was added EDC (569 mg, 2.97 mmol), HOBt (401 mg, 10.6 mmol), formic acid (248 mg, 5.40 mmol), DCM (20 mL), & NMP (2.5 mL). 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) (1.30 g, 2.70 mmol). The reaction mixture was then permitted to stir overnight at room temperature under an atmosphere of nitrogen. The reaction mixture was then 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. The resulting residue was purified by silica gel chromatography 50-90% EtOAc/DCM, then 1-15% IPA/DCM. The appropriate fractions were combined and the solvent was removed in vacuo to give tert-butyl{1-[4-(9-phenyl[1,2,4]triazolo[3,4-f])-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-6b) as a tan solid. MS (M+H)+: observed=492.2, calculated=492.6.

Workup

  1. stirringto stir overnight at room temperature under an atmosphere of nitrogen
  2. washwashed with a saturated solution of sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography 50-90% EtOAc/DCM
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b462e864af7e40919943417004e96e72
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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