1,2-Dichloroethane → HCID 57805489, compound

HRID 2104126Notes

Reaction equation

HRID 2104126 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[N:23][C:24]=4[NH:34][NH2:35])[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:37](Cl)[CH2:38]Cl.[CH3:41][N:42](C=O)C>>[CH2:37]([NH:42][C:41]1[N:23]2[C:24]([C:25]3[CH:26]=[C:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:18]([C:15]4[CH:14]=[CH:13][C:12]([C:8]5([NH:7][C:6](=[O:36])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:11][CH2:10][CH2:9]5)=[CH:17][CH:16]=4)=[N:19][C:20]=3[CH:21]=[CH:22]2)=[N:34][N:35]=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-ece1fa2298db4c0fb22bfea8926dc9ea
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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