Tert-butyl 2-(4-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)ethylcarbamate → 2-(4-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)ethanamine

HRID 2176681Notes

Reaction equation

HRID 2176681 reaction equation
[F:1][C:2]([F:38])([C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[CH:31]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:38][C:2]([F:1])([C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[CH:31]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH2:20])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

Participants

4

Reactant 1

HCID 67503262Tert-butyl 2-(4-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)ethylcarbamate

Product 1

HCID 576909532-(4-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)ethanamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
23 °C

Procedure

A solution of tert-butyl 2-(4-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)ethylcarbamate (70 mg, 136 mol) in DCM (1 mL) and TFA (1 mL) was stirred for 30 min at 23° C. The solvents were then removed under reduced pressure and crude product purified by RP-HPLC eluting with water/ACN (0.1% TFA). The desired collected fractions were then concentrated under reduced pressure and the resulting residue dissolved in MeOH/DCM (5 mL). Solution was then stirred as a suspension with Si-Carbonated (300 mg; 0.2 mmol) for 30 min at 23° C. The solids were then removed by filtration, washed with MeOH (3×1 mL), and filtrate concentrated under reduced pressure. The product was isolated as a white fluffy solid. MS (ESI pos. ion) m/z: 417 (MH+). Calc'd exact mass for C23H18F2N6: 416.

Workup

  1. customThe solvents were then removed under reduced pressure and crude product
  2. custompurified by RP-HPLC
  3. washeluting with water/ACN (0.1% TFA)
  4. customThe desired collected fractions
  5. concentrationwere then concentrated under reduced pressure
  6. dissolutionthe resulting residue dissolved in MeOH/DCM (5 mL)
  7. customThe solids were then removed by filtration
  8. washwashed with MeOH (3×1 mL), and filtrate
  9. concentrationconcentrated under reduced pressure
  10. customThe product was isolated as a white fluffy solid

Sources & evidence

ORD record
ord-e4b94042214d4f4e97a0bb065067dc29
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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