1,2-Dichloroethane → HCID 57805489, compound

HRID 2064448Notes

Reaction equation

HRID 2064448 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].[CH2:37](Cl)[CH2:38]Cl.[CH3:41][N:42](C=O)C>>[CH2:37]([NH:42][C:41]1[N:12]2[C:3]([C:4]3[CH:5]=[C:6]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:7]([C:13]4[CH:18]=[CH:17][C:16]([C:19]5([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]5)=[CH:15][CH:14]=4)=[N:8][C:9]=3[CH:10]=[CH:11]2)=[N:1][N:2]=1)[CH3:38]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 57805468Tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 57805489HCID 57805489, compound

Conditions

Temperature
80 °C

Procedure

To a microwave vial was added {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-6) (51.2 mg, 0.106 mmol), EDC (102 mg, 0.532 mmol) and DMF (0.6 mL). The reaction mixture was heated under microwave irradiation for 5 minutes at 80° C. (high absorption). Acetic acid (0.5 mL) was added and the reaction mixture was heated under microwave irradiation for 5 minutes at 80° C. (high absorption), The resulting residue was purified by reverse phase column chromatography (Sunfire C18) eluting with 5 to 95% acetonitrile/(0.1% TFA/water) gradient. The appropriate fractions were free based by suspending 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-[3-(ethylamino)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)carbamate (3-1) as an off-white solid. HRMS (M+H)+: observed=535.2800, calculated=535.2816.

Workup

  1. custom(high absorption)
  2. additionAcetic acid (0.5 mL) was added
  3. temperaturethe reaction mixture was heated under microwave irradiation for 5 minutes at 80° C.
  4. custom(high absorption)
  5. customThe resulting residue was purified by reverse phase column chromatography (Sunfire C18)
  6. washeluting with 5 to 95% acetonitrile/(0.1% TFA/water) gradient
  7. washwashed with a saturated solution of sodium bicarbonate
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa034d1207a6486c88fe0f2519bdb3bb
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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