Trifluoroacetic acid → 2-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]octan-2-amine

HRID 221979Notes

Reaction equation

HRID 221979 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[C:14]([C:20]5[CH:25]=[CH:24][C:23]([C:26]6([NH:34]C(=O)OC(C)(C)C)[CH2:29][C:28]7([O:33][CH2:32][CH2:31][O:30]7)[CH2:27]6)=[CH:22][CH:21]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:19]3[C:10]([C:11]4[CH:12]=[C:13]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[C:14]([C:20]5[CH:21]=[CH:22][C:23]([C:26]6([NH2:34])[CH2:29][C:28]7([O:33][CH2:32][CH2:31][O:30]7)[CH2:27]6)=[CH:24][CH:25]=5)=[N:15][C:16]=4[CH:17]=[CH:18]3)=[N:9][N:8]=2)[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58229894tert-butyl (2-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]oct-2-yl)carbamate

Product 1

HCID 248095872-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]octan-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]oct-2-yl) (1-11) in DCM (50 mL) was added TFA (50 mL) at rt under N2 for 2 hours. The reaction was quenched with 1N NaOH (650 mL), poured into saturated sodium bicarbonate, extracted with chloroform, dried over sodium sulfate, filtered and concentrated. The crude residue was recrystallized from methanol to give 2-{4-[3-(1-methyl-1/1-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}-5,8-dioxaspiro[3.4]octan-2-amine (1-12) as a white solid. HRMS (M+H)+: observed=530.2315, calculated=530.2299.

Workup

  1. customThe reaction was quenched with 1N NaOH (650 mL)
  2. additionpoured into saturated sodium bicarbonate
  3. extractionextracted with chloroform
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was recrystallized from methanol

Sources & evidence

ORD record
ord-6e93b7569e004f46ab06250dfd3b2997
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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