Hydrochloric Acid → 1-[4-(3-Ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutanamine

HRID 2064458Notes

Reaction equation

HRID 2064458 reaction equation
[CH2:1]([O:3][C:4]1[N:16]2[C:7]([C:8]3[CH:9]=[C:10]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:11]([C:17]4[CH:22]=[CH:21][C:20]([C:23]5([NH:27]C(=O)OC(C)(C)C)[CH2:26][CH2:25][CH2:24]5)=[CH:19][CH:18]=4)=[N:12][C:13]=3[CH:14]=[CH:15]2)=[N:6][N:5]=1)[CH3:2].Cl.CCOC(C)=O>CO.C(Cl)Cl>[CH2:1]([O:3][C:4]1[N:16]2[C:7]([C:8]3[CH:9]=[C:10]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:11]([C:17]4[CH:18]=[CH:19][C:20]([C:23]5([NH2:27])[CH2:24][CH2:25][CH2:26]5)=[CH:21][CH:22]=4)=[N:12][C:13]=3[CH:14]=[CH:15]2)=[N:6][N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 57805453Tert-butyl{1-[4-(3-ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 249642751-[4-(3-Ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {1-[4-(3-ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (9-1) (0.775 g, 0.133 mmol) was dissolved in MeOH (2 mL) and DCM (2 mL), and 4N solution of HCl in EtOAc (10 mL, 40 mmol) was added. The reaction mixture was then permitted to stir at room temperature, capped but not under an atmosphere of nitrogen. After 1 hour the reaction mixture was concentrated in vacuo and 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 then combined, suspended in ethyl acetate, washed with a saturated solution of sodium bicarbonate, water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 1-[4-(3-ethoxy-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutanamine (1-100) as an off-white solid. HRMS (M+H)+: observed=436.215, calculated=436.2132.

Workup

  1. customcapped but not under an atmosphere of nitrogen
  2. concentrationAfter 1 hour the reaction mixture was concentrated in vacuo
  3. customthe resulting residue was purified by reverse phase column chromatography (Sunfire C18)
  4. washeluting with 5 to 95% acetonitrile/(0.1% TFA/water) gradient
  5. washwashed with a saturated solution of sodium bicarbonate, water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bf45c83e6db45a982eaa8fc3678eab0
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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