1,2-Dichloroethane → HCID 57805513, compound

HRID 2064437Notes

Reaction equation

HRID 2064437 reaction equation
[CH2:1](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(O)=O.[NH:18]([C:20]1[N:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[C:23]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:24]([C:30]1[CH:35]=[CH:34][C:33]([C:36]3([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:39][CH2:38][CH2:37]3)=[CH:32][CH:31]=1)=[N:25]2)[NH2:19]>C(OCC)(=O)C.CN1C(=O)CCC1.C(Cl)Cl>[C:48]1([C:23]2[C:24]([C:30]3[CH:35]=[CH:34][C:33]([C:36]4([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:39][CH2:38][CH2:37]4)=[CH:32][CH:31]=3)=[N:25][C:26]3[CH:27]=[CH:28][N:29]4[CH:1]=[N:19][N:18]=[C:20]4[C:21]=3[CH:22]=2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

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-2320f66f884d47d7947732494e3a690c
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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